Search for "allylboration" in Full Text gives 12 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71
Graphical Abstract
Scheme 1: Chemodivergent reactivity observed in copper-catalyzed borylative couplings of allylic gem-dichlori...
Scheme 2: Cu-Bpin-mediated dimerization of 4,4-dichoro-2-butenoic acid derivatives.
Scheme 3: Control experiments.
Scheme 4: Proposed mechanism for the Cu-catalyzed dimerization of 4,4-dichoro-2-butenoic acid derivatives.
Scheme 5: a) KOt-Bu-mediated intramolecular cyclization of 9. b) Direct formation of cyclopropane 20 from gem...
Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51
Graphical Abstract
Scheme 1: Representative transition-metal catalysis for allylic substitution.
Scheme 2: Formation of stereogenic centers in copper-catalyzed allylic alkylation reactions.
Scheme 3: Copper-mediated, stereospecific SN2-selective allylic substitution through retentive transmetalatio...
Scheme 4: ZnCl2-promoted stereospecific SN2' allylic substitution of secondary alkylcopper species via sequen...
Scheme 5: Temperature and time-dependent configurational stability of chiral secondary organocopper species.
Scheme 6: DFT analysis of B–C bond lengths in various boronate complexes and correlation with reactivity.
Scheme 7: Copper-catalyzed stereospecific allylic alkylation of secondary alkylboronic esters via tert-butyll...
Scheme 8: Copper-catalyzed stereospecific allylic alkylation of chiral tertiary alkylboronic esters via adama...
Scheme 9: DFT-calculated energy surface for boron-to-copper transmetalation of either the tert-butyl group or...
Scheme 10: CuH-catalyzed enantioselective allylic substitution and postulated catalytic cycle.
Scheme 11: CuH-catalyzed enantioselective allylic substitution of vinylarenes.
Scheme 12: CuH-catalyzed stereoselective allylic substitution of vinylboronic esters.
Scheme 13: (a) Generation of chiral copper species via enantioselective CuH addition to vinylBpin. (b) Regardi...
Scheme 14: CuH-catalyzed enantioselective allylic substitution of 1‐trifluoromethylalkenes with 18-crown-6.
Scheme 15: CuH-catalyzed enantioselective allylic substitution of terminal alkynes.
Scheme 16: Copper-catalyzed enantiotopic-group-selective allylic substitution of 1,1-diborylalkanes.
Scheme 17: (a) Computational and (b) experimental studies to elucidate the mechanistic details of the enantiot...
Scheme 18: Copper-catalyzed regio-, diastereo- and enantioselective allylic substitution of 1,1-diborylalkanes....
Scheme 19: (a) Experimental and (b) computational studies to understand the stereoselectivities in oxidative a...
Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38
Graphical Abstract
Figure 1: Ring-strain energies of homobicyclic and heterobicyclic alkenes in kcal mol−1. a) [2.2.1]-Bicyclic ...
Figure 2: a) Exo and endo face descriptions of bicyclic alkenes. b) Reactivity comparisons for different β-at...
Scheme 1: Ni-catalyzed ring-opening/cyclization cascade of heterobicyclic alkenes 1 with alkyl propiolates 2 ...
Scheme 2: Ni-catalyzed ring-opening/cyclization cascade of heterobicyclic alkenes 8 with β-iodo-(Z)-propenoat...
Scheme 3: Ni-catalyzed two- and three-component difunctionalizations of norbornene derivatives 15 with alkyne...
Scheme 4: Ni-catalyzed intermolecular three-component difunctionalization of oxabicyclic alkenes 1 with alkyn...
Scheme 5: Ni-catalyzed intermolecular three-component carboacylation of norbornene derivatives 15.
Scheme 6: Photoredox/Ni dual-catalyzed coupling of 4-alkyl-1,4-dihydropyridines 31 with heterobicyclic alkene...
Scheme 7: Photoredox/Ni dual-catalyzed coupling of α-amino radicals with heterobicyclic alkenes 30.
Scheme 8: Cu-catalyzed rearrangement/allylic alkylation of 2,3-diazabicyclo[2.2.1]heptenes 47 with Grignard r...
Scheme 9: Cu-catalyzed aminoboration of bicyclic alkenes 1 with bis(pinacolato)diboron (B2pin2) (53) and O-be...
Scheme 10: Cu-catalyzed borylalkynylation of oxabenzonorbornadiene (30b) with B2pin2 (53) and bromoalkynes 62.
Scheme 11: Cu-catalyzed borylacylation of bicyclic alkenes 1.
Scheme 12: Cu-catalyzed diastereoselective 1,2-difunctionalization of oxabenzonorbornadienes 30 for the synthe...
Scheme 13: Fe-catalyzed carbozincation of heterobicyclic alkenes 1 with arylzinc reagents 74.
Scheme 14: Co-catalyzed addition of arylzinc reagents of norbornene derivatives 15.
Scheme 15: Co-catalyzed ring-opening/dehydration of oxabicyclic alkenes 30 via C–H activation of arenes.
Scheme 16: Co-catalyzed [3 + 2] annulation/ring-opening/dehydration domino reaction of oxabicyclic alkenes 1 w...
Scheme 17: Co-catalyzed enantioselective carboamination of bicyclic alkenes 1 via C–H functionalization.
Scheme 18: Ru-catalyzed cyclization of oxabenzonorbornene derivatives with propargylic alcohols for the synthe...
Scheme 19: Ru-catalyzed coupling of oxabenzonorbornene derivatives 30 with propargylic alcohols and ethers 106...
Scheme 20: Ru-catalyzed ring-opening/dehydration of oxabicyclic alkenes via the C–H activation of anilides.
Scheme 21: Ru-catalyzed of azabenzonorbornadiene derivatives with arylamides.
Scheme 22: Rh-catalyzed cyclization of bicyclic alkenes with arylboronate esters 118.
Scheme 23: Rh-catalyzed cyclization of bicyclic alkenes with dienyl- and heteroaromatic boronate esters.
Scheme 24: Rh-catalyzed domino lactonization of doubly bridgehead-substituted oxabicyclic alkenes with seconda...
Scheme 25: Rh-catalyzed domino carboannulation of diazabicyclic alkenes with 2-cyanophenylboronic acid and 2-f...
Scheme 26: Rh-catalyzed synthesis of oxazolidinone scaffolds 147 through a domino ARO/cyclization of oxabicycl...
Scheme 27: Rh-catalyzed oxidative coupling of salicylaldehyde derivatives 151 with diazabicyclic alkenes 130a.
Scheme 28: Rh-catalyzed reaction of O-acetyl ketoximes with bicyclic alkenes for the synthesis of isoquinoline...
Scheme 29: Rh-catalyzed domino coupling reaction of 2-phenylpyridines 165 with oxa- and azabicyclic alkenes 30....
Scheme 30: Rh-catalyzed domino dehydrative naphthylation of oxabenzonorbornadienes 30 with N-sulfonyl 2-aminob...
Scheme 31: Rh-catalyzed domino dehydrative naphthylation of oxabenzonorbornadienes 30 with arylphosphine deriv...
Scheme 32: Rh-catalyzed domino ring-opening coupling reaction of azaspirotricyclic alkenes using arylboronic a...
Scheme 33: Tandem Rh(III)/Sc(III)-catalyzed domino reaction of oxabenzonorbornadienes 30 with alkynols 184 dir...
Scheme 34: Rh-catalyzed asymmetric domino cyclization and addition reaction of 1,6-enynes 194 and oxa/azabenzo...
Scheme 35: Rh/Zn-catalyzed domino ARO/cyclization of oxabenzonorbornadienes 30 with phosphorus ylides 201.
Scheme 36: Rh-catalyzed domino ring opening/lactonization of oxabenzonorbornadienes 30 with 2-nitrobenzenesulf...
Scheme 37: Rh-catalyzed domino C–C/C–N bond formation of azabenzonorbornadienes 30 with aryl-2H-indazoles 210.
Scheme 38: Rh/Pd-catalyzed domino synthesis of indole derivatives with 2-(phenylethynyl)anilines 212 and oxabe...
Scheme 39: Rh-catalyzed domino carborhodation of heterobicyclic alkenes 30 with B2pin2 (53).
Scheme 40: Rh-catalyzed three-component 1,2-carboamidation reaction of bicyclic alkenes 30 with aromatic and h...
Scheme 41: Pd-catalyzed diarylation and dialkenylation reactions of norbornene derivatives.
Scheme 42: Three-component Pd-catalyzed arylalkynylation reactions of bicyclic alkenes.
Scheme 43: Three-component Pd-catalyzed arylalkynylation reactions of norbornene and DFT mechanistic study.
Scheme 44: Pd-catalyzed three-component coupling N-tosylhydrazones 236, aryl halides 66, and norbornene (15a).
Scheme 45: Pd-catalyzed arylboration and allylboration of bicyclic alkenes.
Scheme 46: Pd-catalyzed, three-component annulation of aryl iodides 66, alkenyl bromides 241, and bicyclic alk...
Scheme 47: Pd-catalyzed double insertion/annulation reaction for synthesizing tetrasubstituted olefins.
Scheme 48: Pd-catalyzed aminocyclopropanation of bicyclic alkenes 1 with 5-iodopent-4-enylamine derivatives 249...
Scheme 49: Pd-catalyzed, three-component coupling of alkynyl bromides 62 and norbornene derivatives 15 with el...
Scheme 50: Pd-catalyzed intramolecular cyclization/ring-opening reaction of heterobicyclic alkenes 30 with 2-i...
Scheme 51: Pd-catalyzed dimer- and trimerization of oxabenzonorbornadiene derivatives 30 with anhydrides 268.
Scheme 52: Pd-catalyzed Catellani-type annulation and retro-Diels–Alder of norbornadiene 15b yielding fused xa...
Scheme 53: Pd-catalyzed hydroarylation and heteroannulation of urea-derived bicyclic alkenes 158 and aryl iodi...
Scheme 54: Access to fused 8-membered sulfoximine heterocycles 284/285 via Pd-catalyzed Catellani annulation c...
Scheme 55: Pd-catalyzed 2,2-bifunctionalization of bicyclic alkenes 1 generating spirobicyclic xanthone deriva...
Scheme 56: Pd-catalyzed Catellani-type annulation and retro-Diels–Alder of norbornadiene (15b) producing subst...
Scheme 57: Pd-catalyzed [2 + 2 + 1] annulation furnishing bicyclic-fused indanes 281 and 283.
Scheme 58: Pd-catalyzed ring-opening/ring-closing cascade of diazabicyclic alkenes 130a.
Scheme 59: Pd-NHC-catalyzed cyclopentannulation of diazabicyclic alkenes 130a.
Scheme 60: Pd-catalyzed annulation cascade generating diazabicyclic-fused indanones 292 and indanols 294.
Scheme 61: Pd-catalyzed skeletal rearrangement of spirotricyclic alkenes 176 towards large polycyclic benzofur...
Scheme 62: Pd-catalyzed oxidative annulation of aromatic enamides 298 and diazabicyclic alkenes 130a.
Scheme 63: Accessing 3,4,5-trisubstituted cyclopentenes 300, 301, 302 via the Pd-catalyzed domino reaction of ...
Scheme 64: Palladacycle-catalyzed ring-expansion/cyclization domino reactions of terminal alkynes and bicyclic...
Scheme 65: Pd-catalyzed carboesterification of norbornene (15a) with alkynes, furnishing α-methylene γ-lactone...
Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129
Graphical Abstract
Scheme 1: Structures of vicinal ketoesters and examples for their typical reactivity.
Scheme 2: Doyle’s diastereoselective intramolecular aldol addition of α,β-diketoester.
Scheme 3: Synthesis of euphorikanin A (16) by intramolecular, nucleophilic addition [6].
Scheme 4: Ketoester cycloisomerization for the synthesis of preussochromone A (24) [10].
Scheme 5: Diastereoselective, intramolecular aldol reaction of an α-ketoester 28 in the synthesis of (−)-preu...
Scheme 6: Synthesis of an α-ketoester through Riley oxidation and its use in an α-ketol rearrangement in the ...
Scheme 7: Azomethine imine cycloaddition towards the synthesis of the proposed structure of palau’amine (44) [19]....
Scheme 8: Intramolecular diastereoselective carbonyl-ene reaction of an α-ketoester in the synthesis of jatro...
Scheme 9: Grignard addition to an α-ketoester and subsequent Friedel–Crafts cyclization in the synthesis of (...
Scheme 10: Diastereoselective addition to an auxiliary modified α-ketoester in the formal synthesis of (+)-cam...
Scheme 11: Intramolecular photoreduction of an α-ketoester in the synthesis of (rac)-isoretronecanol (69) [26].
Scheme 12: α-Ketoester as nucleophile in a Tsuji–Trost reaction in the synthesis of (rac)-corynoxine (76) [27].
Scheme 13: Mannich reaction of an α-ketoester in the synthesis of (+)-gracilamine (83) [28].
Scheme 14: Enantioselective aldol reaction using an α-ketoester in the synthesis of (−)-irofulven (87) [29].
Scheme 15: Allylboration of a mesoxalic acid ester in the synthesis of (+)-awajanomycin (92) [30,31].
Scheme 16: Condensation of a diamine with mesoxolate in the synthesis of (−)-aplaminal (96) [32].
Scheme 17: Synthesis of mesoxalic ester amide 102 and its use in the synthesis of (rac)-cladoniamide G (103) [33].
Scheme 18: The thermodynamically controlled, intramolecular aldol addition of a vic-tricarbonyl compound in th...
Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274
Graphical Abstract
Figure 1: N,N-Dimethyl-L-vancosamine as substructure of kidamycin and pluramycin.
Figure 2: Glycals as relevant scaffolds for constructing aryl C-glycosidic linkage.
Figure 3: Strategy including a ring-closing metathesis of vinyl ethers as key step for the preparation of sev...
Scheme 1: Evans aldol reaction for the preparation of diastereomeric compounds 13a and 13b.
Scheme 2: Alternative preparation of 13b based on a diastereoselective allylboration.
Scheme 3: O-Vinylation-ring-closing metathesis sequence for access to 3-amino glycals.
Scheme 4: Synthesis of key intermediate 23 for the C-3 unbranched amino glycals preparation.
Scheme 5: Access to diastereoisomeric compounds 3 and 4 from 23.
Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159
Graphical Abstract
Figure 1: Initial proposal for the core macrolactone structure (left) and the established complete structure ...
Figure 2: Mycolactone congeners and their origins.
Figure 3: Misassigned mycolactone E structure according to Small et al. [50] (11) and the correct structure (6) f...
Figure 4: Schematic illustration of Kishi’s improved mycolactone TLC detection method exploiting derivatizati...
Figure 5: Fluorescent probes derived from natural mycolactone A/B (1a,b) or its synthetic 8-desmethyl analogs...
Figure 6: Tool compounds used by Pluschke and co-workers for elucidating the molecular targets of mycolactone...
Figure 7: Synthetic strategies towards the extended mycolactone core. A) General strategies. B) Kishi’s appro...
Scheme 1: Kishi’s 1st generation approach towards the extended core structure of mycolactones. Reagents and c...
Scheme 2: Kishi’s 2nd generation approach towards the extended core structure of mycolactones. Reagents and c...
Scheme 3: Kishi’s 3rd generation approach towards the extended core structure of mycolactones. Reagents and c...
Scheme 4: Negishi’s synthesis of the extended core structure of mycolactones. Reagents and conditions: a) (i) ...
Scheme 5: Burkart’s (incomplete) 1st generation approach towards the extended core structure of mycolactones....
Scheme 6: Burkart’s (incomplete) 1st, 2nd and 3rd generation approach towards the extended mycolactone core s...
Scheme 7: Altmann’s synthesis of alkyl iodide 91. Reagents and conditions: a) (i) PMB-trichloroacetimidate, T...
Scheme 8: Final steps of Altmann’s synthesis of the extended core structure of mycolactones. Reagents and con...
Scheme 9: Basic principles of the Aggarwal lithiation–borylation homologation process [185,186].
Scheme 10: Aggarwal’s synthesis of the C1–C11 fragment of the mycolactone core. Reagents and conditions: a) Cl...
Scheme 11: Aggarwal’s synthesis of the linear C1–C20 fragment of the mycolactone core. Reagents and conditions...
Figure 8: Synthetic strategies towards the mycolactone A/B lower side chain.
Scheme 12: Gurjar and Cherian’s synthesis of the C1’–C8’ fragment of the mycolactone A/B pentaenoate side chai...
Scheme 13: Gurjar and Cherian’s synthesis of the benzyl-protected mycolactone A/B pentaenoate side chain. Reag...
Scheme 14: Kishi’s synthesis of model compounds for elucidating the stereochemistry of the C7’–C16’ fragment o...
Scheme 15: Kishi’s synthesis of the mycolactone A/B pentaenoate side chain. (a) (i) NaH, (EtO)2P(O)CH2CO2Et, T...
Scheme 16: Feringa and Minnaard's incomplete synthesis of mycolactone A/B pentaenoate side chain. Reagents and...
Scheme 17: Altmann’s approach towards the mycolactone A/B pentaenoate side chain. Reagents and conditions: a) ...
Scheme 18: Negishi’s access to the C1’–C7’ fragment of mycolactone A. Reagents and conditions: a) (i) n-BuLi, ...
Scheme 19: Negishi’s approach to the C1’–C7’ fragment of mycolactone B. Reagents and conditions: a) (i) DIBAL-...
Scheme 20: Negishi’s synthesis of the C8’–C16’ fragment of mycolactone A/B. Reagents and conditions: a) 142, BF...
Scheme 21: Negishi’s assembly of the mycolactone A and B pentaenoate side chains. Reagents and conditions: a) ...
Scheme 22: Blanchard’s approach to the mycolactone A/B pentaenoate side chain. a) (i) Ph3P=C(Me)COOEt, CH2Cl2,...
Scheme 23: Kishi’s approach to the mycolactone C pentaenoate side chain exemplified for the 13’R,15’S-isomer 1...
Scheme 24: Altmann’s (unpublished) synthesis of the mycolactone C pentaenoate side chain. Reagents and conditi...
Scheme 25: Blanchard’s synthesis of the mycolactone C pentaenoate side chain. Reagents and conditions: a) (i) ...
Scheme 26: Kishi’s synthesis of the tetraenoate side chain of mycolactone F exemplified by enantiomer 165. Rea...
Scheme 27: Kishi’s synthesis of the mycolactone E tetraenoate side chain. Reagents and conditions: a) (i) CH2=...
Scheme 28: Wang and Dai’s synthesis of the mycolactone E tetraenoate side chain. Reagents and conditions: a) (...
Scheme 29: Kishi’s synthesis of the dithiane-protected tetraenoate side chain of the minor oxo-metabolite of m...
Scheme 30: Kishi’s synthesis of the mycolactone S1 and S2 pentaenoate side chains. Reagents and conditions: a)...
Scheme 31: Kishi’s 1st generation and Altmann’s total synthesis of mycolactone A/B (1a,b) and Negishi’s select...
Scheme 32: Kishi’s 2nd generation total synthesis of mycolactone A/B (1a,b). Reagents and conditions: a) 2,4,6...
Scheme 33: Blanchard’s synthesis of the 8-desmethylmycolactone core. Reagents and conditions: a) (i) TsCl, TEA...
Scheme 34: Altmann’s (partially unpublished) synthesis of the C20-hydroxylated mycolactone core. Reagents and ...
Scheme 35: Altmann’s and Blanchard’s approaches towards the 11-isopropyl-8-desmethylmycolactone core. Reagents...
Scheme 36: Blanchard’s synthesis of the saturated variant of the C11-isopropyl-8-desmethylmycolactone core. Re...
Scheme 37: Structure elucidation of photo-mycolactones generated from tetraenoate 224.
Scheme 38: Kishi’s synthesis of the linear precursor of the photo-mycolactone B1 lower side chain. Reagents an...
Scheme 39: Kishi’s synthesis of the photo-mycolactone B1 lower side chain. Reagents and conditions: a) LiTMP, ...
Scheme 40: Kishi’s synthesis of a stabilized lower mycolactone side chain. Reagents and conditions: a) (i) TBD...
Scheme 41: Blanchard’s variation of the C12’,C13’,C15’ stereocluster. Reagents and conditions: a) (i) DIBAL-H,...
Scheme 42: Blanchard’s synthesis of aromatic mycolactone polyenoate side chain analogs. Reagents and condition...
Scheme 43: Small’s partial synthesis of a BODIPY-labeled mycolactone derivative and Demangel’s partial synthes...
Scheme 44: Blanchard’s synthesis of the BODIPY-labeled 8-desmethylmycolactones. Reagents and conditions: a) (i...
Scheme 45: Altmann’s synthesis of biotinylated mycolactones. Reagents and conditions: a) (i) CDI, THF, rt, 2 d...
Figure 9: Kishi’s elongated n-butyl carbamoyl mycolactone A/B analog.
Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19
Graphical Abstract
Scheme 1: 1-Boron-substituted 1,3-diene in a tandem cycloaddition [4 + 2]/allylboration sequence.
Scheme 2: Lewis acid catalyst in the tandem cycloaddition [4 + 2]/allylboration sequence.
Scheme 3: Synthesis of an advanced precursor of clerodin.
Scheme 4: Intramolecular Diels–Alder/allylboration sequence.
Scheme 5: Diastereoselective Diels–Alder reaction with N-phenylmaleimide and 4-phenyltriazoline-3,5-dione.
Scheme 6: Asymmetric synthesis of a α-hydroxyalkylcyclohexane.
Scheme 7: Tandem [4 + 2]-cycloaddition/allylboration of 3-silyloxy- and 4-alkoxy-dienyl boronates.
Scheme 8: Metal-mediated cycloisomerization/Diels–Alder reaction/allylboration sequence.
Scheme 9: Cobalt-catalyzed Diels–Alder/allylboration sequence.
Scheme 10: A two-step reaction sequence for the synthesis of tetrahydronaphthalenes 12.
Scheme 11: Tandem sequence based on the Petasis borono–Mannich reaction as first key step.
Scheme 12: One-pot tandem dimerization/allylboration reaction of 1,3-diene-2-boronate.
Scheme 13: Tandem Diels–Alder/cross-coupling reactions of trifluoroborates 15.
Scheme 14: Diels–Alder/cross-coupling reactions of 16.
Scheme 15: Metal catalyzed tandem Diels–Alder/hydrolysis reactions.
Scheme 16: Synthesis of anti-1,5-diols 18 by triple aldehyde addition.
Scheme 17: Catalytic enantioselective three-component hetero-[4 + 2]-cycloaddition/allylboration sequence.
Scheme 18: Synthesis of natural products using the catalytic enantioselective HDA/allylboration sequence.
Scheme 19: Total synthesis of a thiomarinol derivative.
Scheme 20: Synthesis of an advanced intermediate 27 for the east fragment of palmerolide A.
Scheme 21: Bicyclic piperidines from tandem aza-[4 + 2]-cycloaddition/allylboration.
Scheme 22: Hydrogenolysis reactions of hydrazinopiperidines.
Scheme 23: Tandem aza-[4 + 2]-cycloaddition/allylboration/retrosulfinyl-ene sequence.
Scheme 24: Boronated heterodendralene 32 in [4 + 2]-cycloadditions.
Scheme 25: Synthesis of tricyclic imides derivatives.
Scheme 26: Synthesis of 37 via a HDA/allylboration/DA sequence.
Scheme 27: Diels–Alder/allylboration sequence.
Beilstein J. Org. Chem. 2012, 8, 606–612, doi:10.3762/bjoc.8.67
Graphical Abstract
Scheme 1: Concept for library generation by dipolar cycloaddition followed by boronate coupling.
Scheme 2: General formation of alkyl (R) and aryl (Ar) nitrile oxides.
Scheme 3: Formation of 4-(aldoxime)phenylboronic acid pinacol ester 5.
Beilstein J. Org. Chem. 2011, 7, 1315–1322, doi:10.3762/bjoc.7.154
Graphical Abstract
Figure 1: Chiral diols useful for asymmetric synthesis and the tetralithio intermediate 8.
Scheme 1: Directed ortho,ortho'-dimetalation of (R,R)-hydrobenzoin (3).
Figure 2: Percentage of (R,R)-hydrobenzoin (3) (○), monodeuterohydrobenzoin (13) (■), and dideuterohydrobenzo...
Figure 3: Percentage of methylhydrobenzoin (14) (■), and dimethylhydrobenzoin (15) (Δ) as determined by 1H NM...
Scheme 2: Formation of the tetralithio intermediate 8 and the X-ray crystal structure of the bis(siloxane) 19....
Scheme 3: Reaction of the tetralithio intermediate 8 with various electrophiles.
Scheme 4: Reactions of the diiodohydrobenzoin 12 and X-ray crystal structure of the dihydrosilepin 31.
Scheme 5: Cross coupling reactions of the bis(benzoxaborol) 20 and a short formal synthesis of (R,R)-Vivol (4...
Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48
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.
Beilstein J. Org. Chem. 2007, 3, No. 37, doi:10.1186/1860-5397-3-37
Graphical Abstract
Figure 1: Piclavines A1-A4.
Scheme 1: Enantiomeric enhancement by iterative AD.
Scheme 2: Asymmetric synthesis of indolidines 209D using an iterative AD.
Scheme 3: Asymmetric synthesis of piclavines A1 and A2 from (2R-[4S])-15.
Scheme 4: Asymmetric synthesis of piclavines A3 and A4 from (2R-[4R])-15.
Scheme 5: Asymmetric synthesis of enantiomers of piclavines (1–4).
Beilstein J. Org. Chem. 2005, 1, No. 7, doi:10.1186/1860-5397-1-7
Graphical Abstract
Scheme 1:
Figure 1: Cyclodehydration of diol 2a
Scheme 2:
Figure 2: Cyclodehydration of other diol substrates
Scheme 3:
Scheme 4:
Figure 3: Cyclization of Hydroxymesylates 11