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Search for "diol" in Full Text gives 402 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation

  • Lukáš Ďurina,
  • Anna Ďurinová,
  • František Trejtnar,
  • Ľuboš Janotka,
  • Lucia Messingerová,
  • Jana Doháňošová,
  • Ján Moncol and
  • Róbert Fischer

Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188

Graphical Abstract
  • -stereoselective epoxidation of 2,3-dihydroisoxazole with in situ-generated DMDO, the syn-selective α-chelation-controlled addition of vinyl-MgBr/CeCl3 to the isoxazolidine-4,5-diol intermediate, and the substrate-directed epoxidation of the terminal double bond of the corresponding γ-amino-α,β-diol with aqueous
  • cancer cell lines [14]. For this reason, the compounds 1 and 2 were prepared first in their racemic form to begin the initial biological studies. Results and Discussion The starting isoxazolidine-4,5-diol 3, possessing the desired 3,4-trans configuration (Scheme 1), will be prepared by using our
  • isoxazolidine-4,5-diols in the presence of anhydrous cerium chloride [17], which proceeded in a highly syn-diastereoselective manner due to the presence of the unprotected hydroxy group in the α-position. Accordingly, the diol 3 will be examined in the reaction with vinylmagnesium bromide with an emphasis on
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Published 24 Nov 2021

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Graphical Abstract
  • % aqueous sulfuric acid, the isopropylidene group of 13 was selectively deprotected at 70 °C in dioxane to obtain diol 14. This diol was further cleaved using lead tetraacetate, and further reduction with sodium borohydride produced compound 15. The 5'-hydroxy group of 15 was then treated with tert
  • ). Sodium periodate was used for oxidative cleavage of cis-diol 3d. The subsequent aldehyde was then converted to a vicinal diol by reduction with sodium borohydride. Further, it was protected by 2,2-dimethoxypropane to give the 1,3-oxathiolane derivative 21. The benzoylated compound 22 was obtained by
  • reaction of benzoyl chloride in pyridine to protect the hydroxy group, which results in a high yield. The isopropylidene group was selectively deprotected using 10% HCl, followed by oxidative breakage of the carbon–carbon bond of the resulting diol using sodium periodate. Further reduction of the aldehyde
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Published 04 Nov 2021

α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

  • Scott Benz and
  • Andrew S. Murkin

Beilstein J. Org. Chem. 2021, 17, 2570–2584, doi:10.3762/bjoc.17.172

Graphical Abstract
  • enzymatic base (B), ring opens and subsequently rearranges to 74. AuaH uses NADH to reduce the ketone to diol 75, which undergoes dehydration to give aurachin B (76). The conversion of asperfloroid (73) to asperflotone (72), featuring the ring-expanding α-ketol rearrangement of 74 to form 75. Hypothetical
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Published 15 Oct 2021

Strategies for the synthesis of brevipolides

  • Yudhi D. Kurniawan and
  • A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

Graphical Abstract
  • reduced in a stereoselective manner adopting Luche conditions to provide diol 24 (dr 97:3), which after masking the primary alcohol moiety as a silyl ether, allowed isolation of the desired product 25 in 86% yield. This intermediate possessed the correct chirality on the free secondary alcohol to
  • desired epoxide 30 after one hour in 85% yield (dr 10:1). This species was next converted to the terminal carbonate derivative 31 to transform the epoxy functionality to a vicinal diol through a two-step manipulation involving protection of the terminal alcohol as Boc derivative followed by BF3·Et2O
  • acid (17) (Scheme 4). The β-hydroxy moiety in 44 can be installed via Sharpless dihydroxylation of the silyl enol ether derived from ketone 45. The 5,6-dihydro-α-pyrone group in ketone 45 is envisaged from protected diol 46 by the sequence of Mitsunobu esterification, ring-closing metathesis, and base
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Published 14 Sep 2021

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

  • Sumana Mandal,
  • Raju D. Chaudhari and
  • Goutam Biswas

Beilstein J. Org. Chem. 2021, 17, 2348–2376, doi:10.3762/bjoc.17.153

Graphical Abstract
  • ) [101]. Later it was shown that alkynyl diol 150 when treated with 20 mol % Hg(OTf)2 followed by Et3SiH afforded bispyranoyl ketone 151, but when Hg(OTf)2 was increased (1 equiv) then fused pyran-oxocane derivative 152 was isolated [102]. Six-membered morpholine derivatives were also synthesized by
  • , hippuristanol and some analogs were successfully synthesized utilizing a Hg(OTf)2-catalyzed cascade spiroketalization step of the 3-alkyne-1,7-diol motif. The Hg(OTf)2-catalyzed cascade spiroketalization step was proved to be more convenient than Suárez cyclization. A Hg(TFA)2-mediated cyclization was
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Published 09 Sep 2021

Recent advances in the syntheses of anthracene derivatives

  • Giovanni S. Baviera and
  • Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

Graphical Abstract
  • yields (89–94%) and mild reaction conditions [53]. In a related approach, in 2015, Mohanakrishnan and his group reported the synthesis of anthracene derivatives and other annulated products via the regioselective cyclization of asymmetric 1,2-diarylmethine diol 83b by using a HBr/AcOH system (Scheme 20
  • converted to the substituted anthracenes 109 and 110 by varying the acidic workup procedures. In addition, they prepared 9-chloro-10-phenylanthracene (112) in good yield (87%) through diol 111 [59]. Synthesis of substituted benzo[a]anthracene and dibenzoanthracene derivatives Metal-catalyzed C–H bond
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Published 10 Aug 2021

Progress and challenges in the synthesis of sequence controlled polysaccharides

  • Giulio Fittolani,
  • Theodore Tyrikos-Ergas,
  • Denisa Vargová,
  • Manishkumar A. Chaube and
  • Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

Graphical Abstract
  • resulting 2,3-diol as acceptor in the following glycosylation [131]. A regioselective glycosylation strategy was developed to obtain a collection of linear glucans (8mer to 16mer) (Scheme 4), as well as a branched 9mer and 17mer [137][138]. A similar strategy based on the regioselective glycosylation of a
  • 2,3-diol 4,6-O-benzylidene acceptor permitted to access various β(1–3)-glucans, ranging from trimer to 13mer [126]. Regioselectivity was also achieved using a gold-catalyzed glycosylation, to give a linear β(1–3)-linked 11mer and a branched 14mer in a convergent manner [139]. Collection of linear as
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Published 05 Aug 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

Graphical Abstract
  • [158]. The synthesis started with a cyclopentene derivative, obtained after two steps from a diol via tosylation/displacement strategy with Me2CuLi·LiI. Then, after a Lewis acid-promoted cycloaddition, the alkylation of the α-carbon atom followed by regioselective Baeyer–Villiger oxidation provided the
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Published 30 Jul 2021

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

  • Jana M. Boysen,
  • Nauman Saeed and
  • Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

Graphical Abstract
  • more likely to survive internalization by lung epithelial cells [147][154][155]. Although DHN-melanin is generally associated with immune evasion it was recently found to be recognized in higher animals via the C-type lectin receptor (MelLec) which interacts with the naphthalene-diol domain of DHN
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Published 28 Jul 2021

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

  • Jie Zheng,
  • Shuyu Meng and
  • Quanrui Wang

Beilstein J. Org. Chem. 2021, 17, 1481–1489, doi:10.3762/bjoc.17.104

Graphical Abstract
  • alkynyl-Prins cyclization, Friedel–Crafts alkenylation, and dehydration/aromatization reaction between 1-aryl-3-hexyne-2,6-diol derivatives and aldehydes, that led to the formation of 1,4-dihydro-2H-benzo[f]isochromenes [16]. The Prins reaction-induced cyclization, inter alia, became a versatile tool for
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Published 22 Jun 2021

Total synthesis of ent-pavettamine

  • Memory Zimuwandeyi,
  • Manuel A. Fernandes,
  • Amanda L. Rousseau and
  • Moira L. Bode

Beilstein J. Org. Chem. 2021, 17, 1440–1446, doi:10.3762/bjoc.17.99

Graphical Abstract
  • 1995, was previously identified as a polyamine with C2 symmetry and a 1,3-syn-diol moiety on a C10 carbon backbone – one of very few substituted polyamines to be isolated from nature. Its absolute configuration was later established by our first reported total synthesis in 2010. Herein we report the
  • -pavettamine rather than pavettamine. Chain extension and stereoselective ketone reduction were achieved using the (R)-methyl p-tolyl sulfoxide chiral auxiliary to give the desired 1,3-syn-diol C5 unit. A protecting-group strategy was also developed for the orthogonal protection of the alcohol and amine
  • yield. The first step involved esterification of malic acid using methanol, followed by selective reduction of the resulting dimethyl ester using borane dimethyl sulfide (BMS) yielding diol 5 (Scheme 2) [1][14][15]. The step achieved chemo-differentiation of the carboxyl groups present in 3 whilst
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Published 10 Jun 2021

Double-headed nucleosides: Synthesis and applications

  • Vineet Verma,
  • Jyotirmoy Maity,
  • Vipin K. Maikhuri,
  • Ritika Sharma,
  • Himal K. Ganguly and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Graphical Abstract
  • -headed nucleosides 151a–d starting from LNA uridine diol 147 which in turn was synthesized from diacetone-α-ᴅ-allose following a procedure reported in the literature [76]. LNA uridine diol 147 was reacted with iodine and ceric ammonium nitrate (CAN) in acetic acid to afford the nucleoside 148. Nucleoside
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Published 08 Jun 2021

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

  • Joseane A. Mendes,
  • Paulo R. R. Costa,
  • Miguel Yus,
  • Francisco Foubelo and
  • Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Graphical Abstract
  • trimethylsilyl cyanide (TMSCN) in THF at −10 °C. The reaction product 142 was obtained in quantitative yield and good diastereomeric ratio. Further hydrolysis of the cyclic acetal, and subsequent epoxidation of the resulting diol under typical Mitsunobu conditions led to epoxide derivative 143. The piperidine
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Published 12 May 2021

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

  • Vojtěch Hamala,
  • Lucie Červenková Šťastná,
  • Martin Kurfiřt,
  • Petra Cuřínová,
  • Martin Dračínský and
  • Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

Graphical Abstract
  • thioglycosides 27–31 (Scheme 3). As the 3,4-difluorinated thiogalactoside could not be accessed from compound 13 by reaction with PhSTMS/ZnI2 (Scheme 2), it was necessary to obtain 3,4-difluoro and 3,4,6-trifluoro analogs of GalNAc from 3-fluoro-4,6-diol 18. According to precedents in the literature [53
  • ], deoxyfluorination of the C4-hydroxy group in compound 18 was expected to occur with inversion of configuration to give the desired galacto-configured 4-fluoro products. Accordingly, treatment of diol 18 with DAST resulted in deoxyfluorination of both hydroxy groups to yield trifluoro thiogalactosazide 34 (Scheme 3
  • ). 4,6-O-Benzylidenation of diol 18 followed by regioselective opening of the benzylidene acetal produced compound 35. Subsequent DAST deoxyfluorination delivered the desired thioglycoside 36 (Scheme 3). For both compounds 18 and 35, deoxyfluorination of the C4 hydroxy group occurred with inversion of
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Published 11 May 2021

Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

  • Ákos Bajtel,
  • Mounir Raji,
  • Matti Haukka,
  • Ferenc Fülöp and
  • Zsolt Szakonyi

Beilstein J. Org. Chem. 2021, 17, 983–990, doi:10.3762/bjoc.17.80

Graphical Abstract
  • -amino-1,3-diols, which underwent a regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3. Keywords: 2-amino-1,2-diol; monoterpene; oxazolidin
  • -2-one; stereoselective; tautomerism; Introduction The best known 2-amino-1,3-diol derivative sphingosine (1) plays a crucial role in intracellular signaling as second messenger, and its derivatives called sphingolipids are also critical for cell growth, cell differentiation, cell recognition, and
  • the lack of a readily available natural sources and the high biological importance of sphingolipid analogues, their synthesis has been the subject of numerous studies [16]. The key step for the synthesis is the stereoselective construction of the 2-amino-1,3-diol moiety of the molecules. Generally
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Published 03 May 2021

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

  • Asha Budakoti,
  • Pradip Kumar Mondal,
  • Prachi Verma and
  • Jagadish Khamrai

Beilstein J. Org. Chem. 2021, 17, 932–963, doi:10.3762/bjoc.17.77

Graphical Abstract
  • the synthesis of diol by the condensation of styrene and paraformaldehyde in the presence of a Brønsted acid [23][24]. The major breakthrough for this reaction was reported by Hanschke in 1955, when the THP ring was selectively constructed through a Prins reaction involving 3-butene-1-ol and a variety
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Published 29 Apr 2021

Kinetics of enzyme-catalysed desymmetrisation of prochiral substrates: product enantiomeric excess is not always constant

  • Peter J. Halling

Beilstein J. Org. Chem. 2021, 17, 873–884, doi:10.3762/bjoc.17.73

Graphical Abstract
  • -pong second (ketone amination, diol esterification, desymmetrisation in the second half reaction); ping-pong first (diol ester hydrolysis) and ping-pong both (prochiral diacids). For plausible values of enzyme kinetic parameters, the product enantiomeric excess (ee) can decline substantially as the
  • prochiral diols. The enzyme reacts with an amino or acyl donor, releasing a first co-product, to give an aminated or acylated enzyme intermediate. This then reacts with the prochiral ketone or diol to generate the chiral products. “Ping-pong, first”. Followed in most lipase or esterase hydrolyses of
  • prochiral diol esters. The enzyme reacts enantiospecifically with the ester to release a chiral product, leaving the acyl group attached to the active site. In a second stage the achiral acyl group undergoes hydrolysis by water. In the desymmetrisation of diols (and diacids, below) kinetic amplification can
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Published 21 Apr 2021

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

  • Ke Wu,
  • Yichen Ling,
  • An Ding,
  • Liqun Jin,
  • Nan Sun,
  • Baoxiang Hu,
  • Zhenlu Shen and
  • Xinquan Hu

Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

Graphical Abstract
  • reckoned that converting compound A to a more polar derivative could probably be a breakthrough. As common knowledge, the more polarized alcohols over EtOH are those diols or polyols, while MeOH was previously ruled out. Ethylene glycol, a basic chemical and the simplest diol, is slightly soluble in
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Published 09 Apr 2021

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

  • Emine Salamci and
  • Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

Graphical Abstract
  • are reported. Reduction of cyclooctene endoperoxide, obtained by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc yielded a cyclooctene diol followed by acetylation of the hydroxy group, which gave dioldiacetate by OsO4/NMO oxidation. The cyclooctane dioldiacetate prepared was converted to
  • should have a cis configuration relative to the protons H-3 and H-4. Next, the reduction of azidotriol 10 by hydrogenation afforded the target aminotriol 12 in 95% yield. For the synthesis of the other aminocyclooctanetriol 18, the diol 6a [33] was reacted with m-CPBA to give trans-epoxide isomer 13 [33
  • method for the synthesis of a novel chlorocyclooctanetriol isomer, epoxy-diol 22, which was synthesized in our previous work [31], was hydrolysed by HCl(g) in MeOH, resulting in the formation of two chlorocyclooctanetriol isomers 23 and 24 in an 85:15 ratio (1H NMR) in 96% combined yield (Scheme 5
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Published 11 Mar 2021

Valorisation of plastic waste via metal-catalysed depolymerisation

  • Francesca Liguori,
  • Carmen Moreno-Marrodán and
  • Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

Graphical Abstract
  • )stoichiometric amounts of diol cleaving agents, other than EG (for instance, PD [239], DEG [240][241]). As a consequence, the depolymerisation step usually results in complex mixtures of oligomers. Moreover, reacting diols may be unstable under the reaction conditions adopted. Hence, if used in excess, a
  • chemical recycling to produce novel polyesters [245]. In this process, isosorbide was used as depolymerising diol to give a mixture of differently composed oligomers, whereas succinic acid was added in the second step as polymerising comonomer (Scheme 7). Both steps were efficiently catalysed by
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Published 02 Mar 2021

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

  • Marek Kõllo,
  • Marje Kasari,
  • Villu Kasari,
  • Tõnis Pehk,
  • Ivar Järving,
  • Margus Lopp,
  • Arvi Jõers and
  • Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

Graphical Abstract
  • chemistry and synthetic biology. Stereo- and regioselective hydroxylation at C9 (steroid numbering) is carried out using whole-cell biocatalysis, followed by the chemical cleavage of the C–C bond of the vicinal diol. The two-step method features mild reaction conditions and completely excludes the use of
  • to its toxicity, the oxidation rate affording trans-diols was very slow in comparison to that for cis-diols. Using an even longer reaction time and stoichiometric amount of the reagent, diol 5 was not oxidized to the corresponding dicarbonyl compound 8. However, using NaOCl·5H2O as an oxidant [31
  • ], diols 5 and 6 were effectively converted to the corresponding 9,11-secosterols 8 and 9 within one hour at 0 °C (Scheme 3). Compound 8 was isolated as 2:1 mixture together with starting diol 5 and purified further by preparative TLC. Compound 9 was isolated as a single product in 87% yield. Conclusion We
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Published 01 Mar 2021

The preparation and properties of 1,1-difluorocyclopropane derivatives

  • Kymbat S. Adekenova,
  • Peter B. Wyatt and
  • Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Graphical Abstract
  • [81]. The authors obtained the chiral monoacetate intermediates (R)-78 and (S)-80 by lipase-catalyzed methods. The lipase-catalyzed asymmetric transesterification of prochiral diol 77 and the deacetylation of the prochiral diacetate 79 resulted in the formation of the (R)-monoacetate (R)-78 and (S
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Published 26 Jan 2021

Total synthesis of decarboxyaltenusin

  • Lucas Warmuth,
  • Aaron Weiß,
  • Marco Reinhardt,
  • Anna Meschkov,
  • Ute Schepers and
  • Joachim Podlech

Beilstein J. Org. Chem. 2021, 17, 224–228, doi:10.3762/bjoc.17.22

Graphical Abstract
  • Lewis acid, while the utilization of 1.5 equivalents led to a significant overreaction with the predominant formation of 5-bromobenzene-1,3-diol (59%) together with a smaller amount of the required product 8 (30%). The subsequent protection with the TBS group yielded the known aryl bromide 9a [24] with
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Published 22 Jan 2021

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

  • Minzan Zuo,
  • Krishnasamy Velmurugan,
  • Kaiya Wang,
  • Xueqi Tian and
  • Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

Graphical Abstract
  • ] (“Cyclodextrin–gold nanocluster decorated TiO2 enhances photocatalytic decomposition of organic pollutants” by H. Zhu et al., J. Mater. Chem. A vol. 6, © 2017); permission conveyed through Copyright Clearing Center, Inc. Visible-light-driven conversion of benzyl alcohol to H2 and a vicinal diol or to H2 and
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Published 18 Jan 2021

Progress in the total synthesis of inthomycins

  • Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

Graphical Abstract
  • transformed into (−)-101 using a three-step sequence. Upon iodination of (−)-101 produced iodide (+)-102 in excellent yield. Deiodination of (+)-102 followed by regioselective dihydroxylation with Sharpless’ AD mix-β reagent [64][65] provided diol (−)-103 as a mixture of stereoisomers. Significantly, the diol
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Published 07 Jan 2021
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