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Search for "tartaric acid" in Full Text gives 37 result(s) in Beilstein Journal of Organic Chemistry.
Design and synthesis of hybrid cyclophanes containing thiophene and indole units via Grignard reaction, Fischer indolization and ring-closing metathesis as key steps
- Sambasivarao Kotha,
- Ajay Kumar Chinnam and
- Mukesh E. Shirbhate
Beilstein J. Org. Chem. 2015, 11, 1514–1519, doi:10.3762/bjoc.11.165
- of a mixture of L-(+)-tartaric acid/N,N′-dimethylurea (30:70) was heated to 70 °C to obtain a clear melt. To this melt, 2 mmol of N-methyl-N-phenylhydrazine and 1 mmol of diketone were added at 70 °C. After completion of the reaction (TLC monitoring by mini work up), the reaction mixture was quenched
Graphical Abstract
Figure 1: Retrosynthetic approach to hybrid cyclophane derivative 1.
Scheme 1: Attempted synthesis of thiophenophane derivative 2.
Scheme 2: Synthesis of hybrid cyclophane 1.
Figure 2: The molecular crystal structure of 1 with 50% probability [41].
Scheme 3: Attempted synthesis of thiophenophane derivative 2a.
Scheme 4: Synthesis of cyclophane 1a with a thiophene and an indole moiety.
Hybrid macrocycle formation and spiro annulation on cis-syn-cis-tricyclo[6.3.0.02,6]undeca-3,11-dione and its congeners via ring-closing metathesis
- Sambasivarao Kotha,
- Ajay Kumar Chinnam and
- Rashid Ali
Beilstein J. Org. Chem. 2015, 11, 1123–1128, doi:10.3762/bjoc.11.126
- shown that Weiss–Cook dione 1 [49][50][51] is a useful substrate for double Fischer indolization with a low melting mixture of L-(+)-tartaric acid and N,N′-dimethylurea (L-(+)-TA:DMU) [55] at 70 °C to generate an unusual Cs-symmetric diindole derivative along with the known C2-symmetric diindole [56
Graphical Abstract
Figure 1: Natural and non-natural products containing quinane systems.
Figure 2: Quinane building blocks (1–3) and metathetic catalyst used in our strategy.
Scheme 1: Synthesis of tricyclic diones 5 and 2.
Figure 3: Retrosynthetic approach to aza-polyquinane 6 and spiro-polyquinane 7.
Scheme 2: Synthesis of the diindole derivative 9 Reagents and conditions: (i) TA:DMU, PhNHNH3Cl, 70 °C, 6 h, ...
Scheme 3: Synthesis of the macrocyclic aza-polyquinane derivative 6. Reagents and conditions: (i) NaH, allyl ...
Scheme 4: Synthesis of the spiro-polyquinane 7. Reagents and conditions: (i) NaH, allyl bromide, THF, rt, 24 ...
Scheme 5: General strategy to bis-spirocycles via RCM.
Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
- Carolin Edinger,
- Jörn Kulisch and
- Siegfried R. Waldvogel
Beilstein J. Org. Chem. 2015, 11, 294–301, doi:10.3762/bjoc.11.34
- by enantiomeric resolution employing tartaric acid (see Scheme 2, pathway IV) [43]. By the amount of water in the crystallisation mixture the precipitation of the desired diastereomeric salt can be chosen [44]. Furthermore, we developed a Bouveault–Blanc-type protocol where (−)-menthone oxime is
Graphical Abstract
Scheme 1: Structural features of 8-substituted menthylamines 1.
Scheme 2: Synthetic strategies to menthylamines.
Scheme 3: Stereoselective synthesis of 8-substituted (1R,3R,4S)-menthylamines.
Scheme 4: Influence of the cathode system onto the stereoselectivity of the reduction of (1R,4S)-menthone oxi...
Scheme 5: Preparation of 8-substituted (1R)-menthones 6 and the corresponding oximes 7.
Scheme 6: Influence of cathode material on the preparation of (1R,3R,4S)-menthylamine 8a.
Scheme 7: Protection of the oxime functionality in 7c due to the sterically demanding diphenyl moiety in 8-po...
Scheme 8: Separation of the diastereomeric 8-substituted menthylamines by crystallization of their hydrochlor...
An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles
- Marcus Baumann and
- Ian R. Baxendale
Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265
- ). The required (R)-enantiomer of ethyl nipecotate can in turn be obtained by a number of different methods including the resolution of the racemate using L-(+)-tartaric acid obtained from full saturation of ethyl nicotinate. More modern methods involve a two-step process wherein ethyl nicotinate (2.52
- isolation of enaminoester 2.80 after treatment of the intermediate with ammonium acetate in methanol. The next step involves a very efficient crystallisation-induced dynamic resolution of the racemic material using the non-natural (S,S)-dibenzoyl-D-tartaric acid ((+)-DBTA). It is described that the desired
Graphical Abstract
Scheme 1: Scaled industrial processes for the synthesis of simple pyridines.
Scheme 2: Synthesis of nicotinic acid from 2-methyl-5-ethylpyridine (1.11).
Scheme 3: Synthesis of 3-picoline and nicotinic acid.
Scheme 4: Synthesis of 3-picoline from 2-methylglutarodinitrile 1.19.
Scheme 5: Picoline-based synthesis of clarinex (no yields reported).
Scheme 6: Mode of action of proton-pump inhibitors and structures of the API’s.
Scheme 7: Hantzsch-like route towards the pyridine rings in common proton pump inhibitors.
Figure 1: Structures of rosiglitazone (1.40) and pioglitazone (1.41).
Scheme 8: Synthesis of rosiglitazone.
Scheme 9: Syntheses of 2-pyridones.
Scheme 10: Synthesis and mechanism of 2-pyrone from malic acid.
Scheme 11: Polymer-assisted synthesis of rosiglitazone.
Scheme 12: Synthesis of pioglitazone.
Scheme 13: Meerwein arylation reaction towards pioglitazone.
Scheme 14: Route towards pioglitazone utilising tyrosine.
Scheme 15: Route towards pioglitazone via Darzens ester formation.
Scheme 16: Syntheses of the thiazolidinedione moiety.
Scheme 17: Synthesis of etoricoxib utilising Negishi and Stille cross-coupling reactions.
Scheme 18: Synthesis of etoricoxib via vinamidinium condensation.
Figure 2: Structures of nalidixic acid, levofloxacin and moxifloxacin.
Scheme 19: Synthesis of moxifloxacin.
Scheme 20: Synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane 1.105.
Scheme 21: Synthesis of levofloxacin.
Scheme 22: Alternative approach to the levofloxacin core 1.125.
Figure 3: Structures of nifedipine, amlodipine and clevidipine.
Scheme 23: Mg3N2-mediated synthesis of nifedipine.
Scheme 24: Synthesis of rac-amlodipine as besylate salt.
Scheme 25: Aza Diels–Alder approach towards amlodipine.
Scheme 26: Routes towards clevidipine.
Figure 4: Examples of piperidine containing drugs.
Figure 5: Discovery of tiagabine based on early leads.
Scheme 27: Synthetic sequences to tiagabine.
Figure 6: Structures of solifenacin (2.57) and muscarine (2.58).
Scheme 28: Enantioselective synthesis of solifenacin.
Figure 7: Structures of DPP-4 inhibitors of the gliptin-type.
Scheme 29: Formation of inactive diketopiperazines from cis-rotameric precursors.
Figure 8: Co-crystal structure of carmegliptin bound in the human DPP-4 active site (PDB 3kwf).
Scheme 30: Improved route to carmegliptin.
Figure 9: Structures of lamivudine and zidovudine.
Scheme 31: Typical routes accessing uracil, thymine and cytosine.
Scheme 32: Coupling between pyrimidones and riboses via the Vorbrüggen nucleosidation.
Scheme 33: Synthesis of lamivudine.
Scheme 34: Synthesis of raltegravir.
Scheme 35: Mechanistic studies on the formation of 3.22.
Figure 10: Structures of selected pyrimidine containing drugs.
Scheme 36: General preparation of pyrimidines and dihydropyrimidones.
Scheme 37: Synthesis of imatinib.
Scheme 38: Flow synthesis of imatinib.
Scheme 39: Syntheses of erlotinib.
Scheme 40: Synthesis of erlotinib proceeding via Dimroth rearrangement.
Scheme 41: Synthesis of lapatinib.
Scheme 42: Synthesis of rosuvastatin.
Scheme 43: Alternative preparation of the key aldehyde towards rosuvastatin.
Figure 11: Structure comparison between nicotinic acetylcholine receptor agonists.
Scheme 44: Syntheses of varenicline and its key building block 4.5.
Scheme 45: Synthetic access to eszopiclone and brimonidine via quinoxaline intermediates.
Figure 12: Bortezomib bound in an active site of the yeast 20S proteasome ([114], pdb 2F16).
Scheme 46: Asymmetric synthesis of bortezomib.
Figure 13: Structures of some prominent piperazine containing drugs.
Figure 14: Structural comparison between the core of aplaviroc (4.35) and a type-1 β-turn (4.36).
Scheme 47: Examplary synthesis of an aplaviroc analogue via the Ugi-MCR.
Scheme 48: Syntheses of azelastine (5.1).
Figure 15: Structures of captopril, enalapril and cilazapril.
Scheme 49: Synthesis of cilazapril.
Figure 16: Structures of lamotrigine, ceftriaxone and azapropazone.
Scheme 50: Synthesis of lamotrigine.
Scheme 51: Alternative synthesis of lamotrigine (no yields reported).
Figure 17: Structural comparison between imiquimod and the related adenosine nucleoside.
Scheme 52: Conventional synthesis of imiquimod (no yields reported).
Scheme 53: Synthesis of imiquimod.
Scheme 54: Synthesis of imiquimod via tetrazole formation (not all yields reported).
Figure 18: Structures of various anti HIV-medications.
Scheme 55: Synthesis of abacavir.
Figure 19: Structures of diazepam compared to modern replacements.
Scheme 56: Synthesis of ocinaplon.
Scheme 57: Access to zaleplon and indiplon.
Scheme 58: Different routes towards the required N-methylpyrazole 6.65 of sildenafil.
Scheme 59: Polymer-supported reagents in the synthesis of key aminopyrazole 6.72.
Scheme 60: Early synthetic route to sildenafil.
Scheme 61: Convergent preparations of sildenafil.
Figure 20: Comparison of the structures of sildenafil, tadalafil and vardenafil.
Scheme 62: Short route to imidazotriazinones.
Scheme 63: Alternative route towards vardenafils core imidazotriazinone (6.95).
Scheme 64: Bayer’s approach to the vardenafil core.
Scheme 65: Large scale synthesis of vardenafil.
Scheme 66: Mode of action of temozolomide (6.105) as methylating agent.
Scheme 67: Different routes to temozolomide.
Scheme 68: Safer route towards temozolomide.
Figure 21: Some unreported heterocyclic scaffolds in top market drugs.
Asymmetric synthesis of host-directed inhibitors of myxoviruses
- Terry W. Moore,
- Kasinath Sana,
- Dan Yan,
- Pahk Thepchatri,
- John M. Ndungu,
- Manohar T. Saindane,
- Mark A. Lockwood,
- Michael G. Natchus,
- Dennis C. Liotta,
- Richard K. Plemper,
- James P. Snyder and
- Aiming Sun
Beilstein J. Org. Chem. 2013, 9, 197–203, doi:10.3762/bjoc.9.23
- ) had the poorest antiviral activity (i.e., 18a and 18e, Table 1). To explore the possibility of increasing solubility by salt formation, the L-tartaric acid salt and benzenesulfonic acid salts of the most active compound 18f were synthesized (Figure 3) and subjected to solubility testing. However
- )- (left, magenta) and (R)- (right, cyan) enantiomers of 1. L-Tartaric acid salt (18f-tartrate) and benzenesulfonic acid salt (18f-benzenesulfonate) of 18f. Synthesis of anilino nitrobenzene 7a. Preparation of morpholinyl-o-nitroanilines. Asymmetric synthesis of (R)- and (S)-isomers by using two different
Graphical Abstract
Figure 1: Structure of first-generation lead compound 1.
Scheme 1: Synthesis of anilino nitrobenzene 7a.
Scheme 2: Preparation of morpholinyl-o-nitroanilines.
Scheme 3: Asymmetric synthesis of (R)- and (S)-isomers by using two different approaches.
Scheme 4: Preparation of chiral propionamides by HATU-mediated coupling (a) or thionyl chloride-mediated coup...
Figure 2: Renderings of crystal structures of (S)- (left, magenta) and (R)- (right, cyan) enantiomers of 1.
Figure 3: L-Tartaric acid salt (18f-tartrate) and benzenesulfonic acid salt (18f-benzenesulfonate) of 18f.
Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics
- Marco Marradi,
- Stefano Cicchi,
- Francesco Sansone,
- Alessandro Casnati and
- Andrea Goti
Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107
- -tartaric acid) [28], and its functional groups (an anchoring amine and two transformable hydroxy groups) make it a convenient chiral AB2 building block for the construction of dendrimers [29]. The linkable hydroxy groups of the pyrrolidine rings open up the possibility of constructing calixarene-based
Graphical Abstract
Figure 1: First (2) and second (3) generation of dendrimers based on chiral C2-symmetric pyrrolidine 1 and ha...
Scheme 1: Use of the key intermediate (3S,4S)-1-benzyl-3,4-dihydroxypyrrolidine (6) [31] for the synthesis of pyr...
Scheme 2: Synthesis of calixarene-based dendrimers 2 and 3. Reagents and conditions: DIPEA, CH2Cl2, 30 °C, 5 ...
Figure 2: Expansion (about 7 to 3 ppm) of the 1H NMR spectra of (A) the free ligand 2, (B) the sodium picrate...
Figure 3: Schematic of the inclusion of alkali-metal ions (sodium and potassium) in the polar cavity defined ...
A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
- Nianhong Lu,
- Lihong Wang,
- Zhanshan Li and
- Wei Zhang
Beilstein J. Org. Chem. 2012, 8, 192–200, doi:10.3762/bjoc.8.21
- -alkenylboronates with 2-ethoxy-N-acylquinolines catalyzed by tartaric acid to produce 2-(1-alkenyl)-N-acylquinolines in 2011 [23]. We report here a concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the cross-coupling reactions of N-acyliminium ions derived from 3-hydroxyisoindol
Graphical Abstract
Scheme 1: Reaction of 3-hydroxyisoindol-1-one with styrene.
Scheme 2: Reaction of 5-hydroxypyrrol-1-one with styrene.
Scheme 3: Reactions of 5-hydroxyisoindol-1-ones with olefins in the presence of BF3·OEt2.
Figure 1: X-Ray structure (ORTEP drawing) of 3h.
Scheme 4: Reactions of 5-hydroxypyrrol-1-ones with olefins in the presence of BF3·OEt2.
An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals
- Marcus Baumann,
- Ian R. Baxendale,
- Steven V. Ley and
- Nikzad Nikbin
Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57
Graphical Abstract
Figure 1: Structures of atorvastatin and other commercial statins.
Figure 2: Structure of compactin.
Scheme 1: Synthesis of pentasubstituted pyrroles.
Scheme 2: [3 + 2] Cycloaddition to prepare 5-isopropylpyrroles.
Scheme 3: Regiospecific [3 + 2] cycloaddition to prepare the pyrrole scaffold.
Scheme 4: Formation of the pyrrole core of atorvastatin via [3 + 2] cycloaddition.
Scheme 5: Formation of pyrrole 33 via the Paal–Knorr reaction.
Scheme 6: Convergent synthesis towards atorvastatin.
Figure 3: Binding pocket of sunitinib in the TRK KIT.
Scheme 7: Synthesis of sunitinib.
Scheme 8: Alternative synthesis of sunitinib.
Scheme 9: Key steps in the syntheses of sumatriptan and zolmitriptan.
Scheme 10: Introduction of the N,N-dimethylaminoethyl side chain.
Scheme 11: Japp–Klingemann reaction in the synthesis of sumatriptan.
Scheme 12: Synthesis of the intermediate sulfonyl chlorides 62 and 63.
Scheme 13: Alternative introduction of the sulfonamide.
Scheme 14: Negishi-type coupling to benzylic sulfonamides.
Scheme 15: Heck reaction used to introduce the sulfonamide side chain of naratriptan.
Scheme 16: Synthesis of the oxazolinone appendage of zolmitriptan.
Scheme 17: Grandberg indole synthesis used in the preparation of rizatriptan.
Scheme 18: Improved synthesis of rizatriptan.
Scheme 19: Larock-type synthesis of rizatriptan.
Scheme 20: Synthesis of eletriptan.
Scheme 21: Heck coupling for the indole system in eletriptan.
Scheme 22: Attempted Fischer indole synthesis of elatriptan.
Scheme 23: Successful Fischer indole synthesis for eletriptan.
Scheme 24: Mechanistic rationale for the Bischler–Möhlau reaction.
Scheme 25: Bischler-type indole synthesis used in the fluvastatin sodium synthesis.
Scheme 26: Palladium-mediated synthesis of ondansetron.
Scheme 27: Fischer indole synthesis of ondansetron.
Scheme 28: Optimised Pictet–Spengler reaction towards tadalafil.
Figure 4: Structures of carvedilol 136 and propranolol 137.
Scheme 29: Synthesis of the carbazole core of carvedilol.
Scheme 30: Alternative syntheses of 4-hydroxy-9H-carbazole.
Scheme 31: Convergent synthesis of etodolac.
Scheme 32: Alternative synthesis of etodolac.
Figure 5: Structures of imidazole-containing drugs.
Scheme 33: Synthesis of functionalised imidazoles towards losartan.
Scheme 34: Direct synthesis of the chlorinated imidazole in losartan.
Scheme 35: Synthesis of trisubstituted imidazoles.
Scheme 36: Preparation of the imidazole ring in olmesartan.
Scheme 37: Synthesis of ondansetron.
Scheme 38: Alternative route to ondansetron and its analogues.
Scheme 39: Proton pump inhibitors and synthesis of esomeprazole.
Scheme 40: Synthesis of benzimidazole core pantoprazole.
Figure 6: Structure of rabeprazole 194.
Scheme 41: Synthesis of candesartan.
Scheme 42: Alternative access to the candesartan key intermediate 216.
Scheme 43: .Medicinal chemistry route to telmisartan.
Scheme 44: Improved synthesis of telmisartan.
Scheme 45: Synthesis of zolpidem.
Scheme 46: Copper-catalysed 3-component coupling towards zolpidem.
Figure 7: Structure of celecoxib.
Scheme 47: Preparation of celecoxib.
Scheme 48: Alternative synthesis of celecoxib.
Scheme 49: Regioselective access to celecoxib.
Scheme 50: Synthesis of pazopanib.
Scheme 51: Syntheses of anastrozole, rizatriptan and letrozole.
Scheme 52: Regioselective synthesis of anastrozole.
Scheme 53: Triazine-mediated triazole formation towards anastrozole.
Scheme 54: Alternative routes to 1,2,4-triazoles.
Scheme 55: Initial synthetic route to sitagliptin.
Figure 8: Binding of sitagliptin within DPP-IV.
Scheme 56: The process route to sitagliptin key intermediate 280.
Scheme 57: Synthesis of maraviroc.
Scheme 58: Synthesis of alprazolam.
Scheme 59: The use of N-nitrosoamidine derivatives in the preparation of fused benzodiazepines.
Figure 9: Structures of itraconazole, ravuconazole and voriconazole.
Scheme 60: Synthesis of itraconazole.
Scheme 61: Synthesis of rufinamide.
Scheme 62: Representative tetrazole formation in valsartan.
Figure 10: Structure of tetrazole containing olmesartan, candesartan and irbesartan.
Scheme 63: Early stage introduction of the tetrazole in losartan.
Scheme 64: Synthesis of cilostazol.
Figure 11: Structure of cefdinir.
Scheme 65: Semi-synthesis of cefdinir.
Scheme 66: Thiazole syntheses towards ritonavir.
Scheme 67: Synthesis towards pramipexole.
Scheme 68: Alternative route to pramipexole.
Scheme 69: Synthesis of famotidine.
Scheme 70: Efficient synthesis of the hyperuricemic febuxostat.
Scheme 71: Synthesis of ziprasidone.
Figure 12: Structure of mometasone.
Scheme 72: Industrial access to 2-furoic acid present in mometasone.
Scheme 73: Synthesis of ranitidine from furfuryl alcohol.
Scheme 74: Synthesis of nitrofurantoin.
Scheme 75: Synthesis of benzofuran.
Scheme 76: Synthesis of amiodarone.
Scheme 77: Synthesis of raloxifene.
Scheme 78: Alternative access to the benzo[b]thiophene core of raloxifene.
Scheme 79: Gewald reaction in the synthesis of olanzapine.
Scheme 80: Alternative synthesis of olanzapine.
Figure 13: Access to simple thiophene-containing drugs.
Scheme 81: Synthesis of clopidogrel.
Scheme 82: Pictet–Spengler reaction in the preparation of tetrahydrothieno[3,2-c]pyridine (422).
Scheme 83: Alternative synthesis of key intermediate 422.
Figure 14: Co-crystal structures of timolol (left) and carazolol (right) in the β-adrenergic receptor.
Scheme 84: Synthesis of timolol.
Scheme 85: Synthesis of tizanidine 440.
Scheme 86: Synthesis of leflunomide.
Scheme 87: Synthesis of sulfamethoxazole.
Scheme 88: Synthesis of risperidone.
Figure 15: Relative abundance of selected transformations.
Figure 16: The abundance of heterocycles within top 200 drugs (5-membered rings).
Rh-Catalyzed rearrangement of vinylcyclopropane to 1,3-diene units attached to N-heterocycles
- Franca M. Cordero,
- Carolina Vurchio,
- Stefano Cicchi,
- Armin de Meijere and
- Alberto Brandi
Beilstein J. Org. Chem. 2011, 7, 298–303, doi:10.3762/bjoc.7.39
- the enantiopure nitrone 10 [42] derived from L-tartaric acid was complete within only 1.5 h at 120–125 °C under microwave (MW) heating and afforded the oxospirocyclopropanes anti-12 and syn-12 in 55% overall yield along with the 1,5-hydrogen shift product 13 (13%) (Scheme 3, see Supporting Information
Graphical Abstract
Scheme 1: General approach to spirocyclopropanated tetrahydropyridones by 1,3-dipolar cycloaddition/thermal r...
Scheme 2: Synthesis of tetrahydrospiro[cyclopropane-1,1’(2’H,6’H)-pyrido[2,1-a]isoquinolin]-2’-one 8.
Scheme 3: Synthesis of 7’-oxohexahydro spiro[cyclopropane-1-8’(5’H)indolizines] 12.
Scheme 4: Olefination of spirocyclopropanated heterocyclic ketones 8, 12 and 16.
Figure 1: Key NOE interactions. 18: 11b-H/11-H, 11b-H/6-H, 11b-H/Ht, Hv/2-CH3; E-19: Hb/CH3, Hc/11b-H, Hc/11-...
Scheme 5: Rearrangement of VCPs 15 and 17 catalyzed by Rh(PPh3)3Cl.
Scheme 6: Mechanism of the rearrangement of heterocyclic VCPs catalyzed by Rh(PPh3)3Cl.
Quinoline based receptor in fluorometric discrimination of carboxylic acids
- Kumaresh Ghosh,
- Suman Adhikari,
- Asoke P. Chattopadhyay and
- Purnendu Roy Chowdhury
Beilstein J. Org. Chem. 2008, 4, No. 52, doi:10.3762/bjoc.4.52
- reduced. The change in absorbance with complex concentration is found to be linear (Figure 4, right side). Figure 5 indicates the case of 1 with D-(−)-tartaric acid where a similar nature of interaction is attributed. These changes in the UV-vis spectra were used conveniently to study the binding since
- the same guests were carried out in CHCl3. The change in absorbance of the complexes of 2 with the acid guests on dilution with CHCl3 was linear in each case. Figure 6 and Figure 7, for example, demonstrate the changes in absorbance of the 1:1 complexes of citric acid and D-(−)-tartaric acid
- -(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absorbance on dilution (left side); plot of absorbance vs. concentration of the complex of D-(−)-tartaric acid with 1 (right side). UV spectra of the complex of 2 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on dilution (left side
Graphical Abstract
Figure 1: Structures of compounds 1 and 2.
Scheme 1: Syntheses of receptors 1 and 2.
Figure 2: UV-vis spectra of 1 (c = 5.05 × 10−5 M) in different solvents.
Figure 3: UV-vis spectra of 2 (c = 5.05 × 10−5 M) in different solvents.
Figure 4: UV spectra of the complex of 1 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on...
Figure 5: UV spectra of the complex of 1 with D-(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absor...
Figure 6: UV spectra of the complex of 2 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on...
Figure 7: UV spectra of the complex of 2 with D-(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absor...
Figure 8: Fluorescence change of 1 in CHCl3 in the presence of carboxylic acids (λex = 290 nm).
Figure 9: Plot of the ratio of excimer to monomer emission vs concentration of the complex of 1 with citric a...
Figure 10: Fluorescence change of 1 in CHCl3 (c = 1.67 × 10−5 M) upon addition of citric acid dissolved in CHCl...
Figure 11: Fluorescence change of 1 in CHCl3 (c = 1.67 × 10−5 M) upon addition of D-(−)-tartaric acid dissolve...
Figure 12: Fluorescence change of 2 in CHCl3 in the presence of carboxylic acids (λex = 290 nm).
Figure 13: Fluorescence change of 2 in CHCl3 (c = 1.67 × 10−5 M) upon addition citric acid dissolved in CHCl3 ...
Figure 14: 1H NMR (in CDCl3) spectra of receptor 1 (c = 3.57 × 10−3 M; bottom) and the 1:1 complex with citric...
Figure 15: AM1 optimized geometries of the complexes of 1 with (a) citric acid, hydrogen bond distances: a = 2...
Figure 16: AM1 optimized geometry of the complex of 2 with citric acid, hydrogen bond distances: a = 2.12 Å, b...
Recent progress on the total synthesis of acetogenins from Annonaceae
- Nianguang Li,
- Zhihao Shi,
- Yuping Tang,
- Jianwei Chen and
- Xiang Li
Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48
- materials (e.g. amino acids, sugars, tartaric acid, etc.) or on asymmetric reactions {e.g. Sharpless asymmetric epoxidation (AE), Sharpless asymmetric dihydroxylation (AD), diastereoselective Williamson etherification, etc.}. Semi-synthesis of natural ACGs as well as derivatised ACGs (e.g. amines, esters
Graphical Abstract
Scheme 1: Total synthesis of longifolicin by Marshall’s group.
Scheme 2: Total synthesis of corossoline by Tanaka’s group.
Scheme 3: Total synthesis of corossoline by Wu’s group.
Scheme 4: Total synthesis of pseudo-annonacin A by Hanessian’s group.
Scheme 5: Total synthesis of tonkinecin by Wu’s group.
Scheme 6: Total synthesis of gigantetrocin A by Shi’s group.
Scheme 7: Total synthesis of annonacin by Wu’s group.
Scheme 8: Total synthesis of solamin by Kitahara’s group.
Scheme 9: Total synthesis of solamin by Mioskowski’s group.
Scheme 10: Total synthesis of cis-solamin by Makabe’s group.
Scheme 11: Total synthesis of cis-solamin by Brown’s group.
Scheme 12: The formal synthesis of (+)-cis-solamin by Donohoe’s group.
Scheme 13: Total synthesis of cis-solamin by Stark’s group.
Scheme 14: Total synthesis of mosin B by Tanaka’s group.
Scheme 15: Total synthesis of longicin by Hanessian’s group.
Scheme 16: Total synthesis of murisolin and 16,19-cis-murisolin by Tanaka’s group.
Scheme 17: Synthesis of a stereoisomer library of (+)-murisolin by Curran’s group.
Scheme 18: Total synthesis of murisolin by Makabe’s group.
Scheme 19: Total synthesis of reticulatain-1 by Makabe’s group.
Scheme 20: Total synthesis of muricatetrocin C by Ley’s group.
Scheme 21: Total synthesis of (4R,12S,15S,16S,19R,20R,34S)-muricatetrocin (146) and (4R,12R,15S,16S,19R,20R,34S...
Scheme 22: Total synthesis of parviflorin by Hoye’s group.
Scheme 23: Total synthesis of parviflorin by Trost’s group.
Scheme 24: Total synthesis of trilobacin by Sinha’s group.
Scheme 25: Total synthesis of 15-epi-annonin I 181b by Scharf’s group.
Scheme 26: Total synthesis of squamocin A and squamocin D by Scharf’s group.
Scheme 27: Total synthesis of asiminocin by Marshall’s group.
Scheme 28: Total synthesis of asiminecin by Marshall’s group.
Scheme 29: Total synthesis of (+)-(30S)-bullanin by Marshall’s group.
Scheme 30: Total synthesis of uvaricin by the group of Sinha and Keinan.
Scheme 31: Formal synthesis of uvaricin by Burke’s group.
Scheme 32: Total synthesis of trilobin by Marshall’s group.
Scheme 33: Total synthesis of trilobin by the group of Sinha and Keinan.
Scheme 34: Total synthesis of asimilobin by the group of Wang and Shi.
Scheme 35: Total synthesis of squamotacin by the group of Sinha and Keinan.
Scheme 36: Total synthesis of asimicin by Marshall’s group.
Scheme 37: Total synthesis of asimicin by the group of Sinha and Keinan.
Scheme 38: Total synthesis of asimicin by Roush’s group.
Scheme 39: Total synthesis of asimicin by Marshall’s group.
Scheme 40: Total synthesis of 10-hydroxyasimicin by Ley’s group.
Scheme 41: Total synthesis of asimin by Marshall’s group.
Scheme 42: Total synthesis of bullatacin by the group of Sinha and Keinan.
Scheme 43: Total synthesis of bullatacin by Roush’s group.
Scheme 44: Total synthesis of bullatacin by Pagenkopf’s group.
Scheme 45: Total synthesis of rollidecins C and D by the group of Sinha and Keinan.
Scheme 46: Total synthesis of 30(S)-hydroxybullatacin by Marshall’s group.
Scheme 47: Total synthesis of uvarigrandin A and 5(R)-uvarigrandin A by Marshall’s group.
Scheme 48: Total synthesis of membranacin by Brown’s group.
Scheme 49: Total synthesis of membranacin by Lee’s group.
Scheme 50: Total synthesis of rolliniastatin 1 and rollimembrin by Lee’s group.
Scheme 51: Total synthesis of longimicin D by the group of Maezaki and Tanaka.
Scheme 52: Total synthesis of the structure proposed for mucoxin by Borhan’s group.
Scheme 53: Modular synthesis of adjacent bis-THF annonaceous acetogenins by Marshall’s group.
Scheme 54: Total synthesis of 4-deoxygigantecin by Tanaka’s group.
Scheme 55: Total synthesis of squamostatins D by Marshall’s group.
Scheme 56: Total synthesis of gigantecin by Crimmins’s group.
Scheme 57: Total synthesis of gigantecin by Hoye’s group.
Scheme 58: Total synthesis of cis-sylvaticin by Donohoe’s group.
Scheme 59: Total synthesis of 17(S),18(S)-goniocin by Sinha’s group.
Scheme 60: Total synthesis of goniocin and cyclogoniodenin T by the group of Sinha and Keinan.
Scheme 61: Total synthesis of jimenezin by Takahashi’s group.
Scheme 62: Total synthesis of jimenezin by Lee’s group.
Scheme 63: Total synthesis of jimenezin by Hoffmann’s group.
Scheme 64: Total synthesis of muconin by Jacobsen’s group.
Scheme 65: Total synthesis of (+)-muconin by Kitahara’s group.
Scheme 66: Total synthesis of muconin by Takahashi’s group.
Scheme 67: Total synthesis of muconin by the group of Yoshimitsu and Nagaoka.
Scheme 68: Total synthesis of mucocin by the group of Sinha and Keinan.
Scheme 69: Total synthesis of mucocin by Takahashi’s group.
Scheme 70: Total synthesis of (−)-mucocin by Koert’s group.
Scheme 71: Total synthesis of mucocin by the group of Takahashi and Nakata.
Scheme 72: Total synthesis of mucocin by Evans’s group.
Scheme 73: Total synthesis of mucocin by Mootoo’s group.
Scheme 74: Total synthesis of (−)-mucocin by Crimmins’s group.
Scheme 75: Total synthesis of pyranicin by the group of Takahashi and Nakata.
Scheme 76: Total synthesis of pyranicin by Rein’s group.
Scheme 77: Total synthesis of proposed pyragonicin by the group of Takahashi and Nakata.
Scheme 78: Total synthesis of pyragonicin by Rein’s group.
Scheme 79: Total synthesis of pyragonicin by Takahashi’s group.
Scheme 80: Total synthesis of squamostanal A by Figadère’s group.
Scheme 81: Total synthesis of diepomuricanin by Tanaka’s group.
Scheme 82: Total synthesis of (−)-muricatacin [(R,R)-373a] and its enantiomer (+)-muricatacin [(S,S)-373b] by ...
Scheme 83: Total synthesis of epi-muricatacin (+)-(S,R)-373c and (−)-(R,S)-373d by Scharf’s group.
Scheme 84: Total synthesis of (−)-muricatacin 373a and 5-epi-(−)-muricatacin 373d by Uang’s group.
Scheme 85: Total synthesis of four stereoisomers of muricatacin by Yoon’s group.
Scheme 86: Total synthesis of (+)-muricatacin by Figadère’s group.
Scheme 87: Total synthesis of (+)-epi-muricatacin and (−)-muricatacin by Couladouros’s group.
Scheme 88: Total synthesis of muricatacin by Trost’s group.
Scheme 89: Total synthesis of (−)-(4R,5R)-muricatacin by Heck and Mioskowski’s group.
Scheme 90: Total synthesis of muricatacin (−)-373a by the group of Carda and Marco.
Scheme 91: Total synthesis of (−)- and (+)-muricatacin by Popsavin’s group.
Scheme 92: Total synthesis of (−)-muricatacin by the group of Bernard and Piras.
Scheme 93: Total synthesis of (−)-muricatacin by the group of Yoshimitsu and Nagaoka.
Scheme 94: Total synthesis of (−)-muricatacin by Quinn’s group.
Scheme 95: Total synthesis of montecristin by Brückner’s group.
Scheme 96: Total synthesis of (−)-acaterin by the group of Franck and Figadère.
Scheme 97: Total synthesis of (−)-acaterin by Singh’s group.
Scheme 98: Total synthesis of (−)-acaterin by Kumar’s group.
Scheme 99: Total synthesis of rollicosin by Quinn’s group.
Scheme 100: Total synthesis of Rollicosin by Makabe’s group.
Scheme 101: Total synthesis of squamostolide by Makabe’s group.
Scheme 102: Total synthesis of tonkinelin by Makabe’s group.
C2- symmetric bisamidines: Chiral Brønsted bases catalysing the Diels- Alder reaction of anthrones
- Deniz Akalay,
- Gerd Dürner,
- Jan W. Bats and
- Michael W. Göbel
Beilstein J. Org. Chem. 2008, 4, No. 28, doi:10.3762/bjoc.4.28
- extraction in the presence of Na2CO3 afforded the neutral bases 8b–c and ent-8d in almost quantitative yield. The S,S configurated diamines 9b and 9c were prepared from L-(+)-tartaric acid (R,R) via the vicinal diazide using Saalfrank's procedure [9]. 9d was purchased as the dihydrochloride salt and then
Graphical Abstract
Scheme 1: Diels-Alder reaction of anthrones 1 and maleimides 2 catalyzed by chiral Brønsted bases 4–8.
Scheme 2: Protonation states and tautomerism of C2-symmetric bisamidine 8a [6].
Scheme 3: Synthesis of C2-symmetric bisamidines 8b–c and ent-8d.
Figure 1: Kinetic measurements of 1a with 2a catalyzed by 5 mol% of 8a·H+·TFPB- (black line) and 1 mol% 8a (f...
Figure 2: Molecular structure of 3m (C: black; N: blue; O: red; Cl: green; hydrogen atoms are omitted for the...
Scheme 4: Proposed mechanism of the Diels-Alder reaction.
