Enantioselective Synthesis of (+)-(2R,3S,6R)-Decarestrictine L

Solladié, Guy; Arce, Eva; Bauder, and Claude; Carreño, M. Carmen

doi:10.1021/jo972187r

Cited by 24 publications

(13 citation statements)

References 34 publications

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“…Methyl ester 5 is obtained in four steps from L -malic acid as described by Solladié and coworkers. 19 Dibal-H reduction of 5 provided the corresponding aldehyde. Wittig olefination of the resulting aldehyde in MeOH at 0 °C afforded α,β-unsaturated ester 6 in 70% yield as a mixture (8:1) of cis / trans isomers.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, biological evaluation and X-ray structural studies of HIV-1 protease inhibitors containing substituted fused-tetrahydropyranyl tetrahydrofuran as P2-ligands

et al. 2015

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Design, synthesis, biological and X-ray crystallographic studies of a series of potent HIV-1 protease inhibitors are described. Various polar functionalities have been incorporated on the tetrahydropyranyl-tetrahydrofuran-derived P2 ligand to interact with the backbone atoms in the S2 subsite. The majority of the inhibitors showed very potent enzyme inhibitory and antiviral activity. Two high-resolution X-ray structures of 30b- and 30j-bound HIV-1 protease provide insight into ligand-binding site interactions. In particular, the polar functionalities on the P2 ligand appear to form unique hydrogen bonds with Gly48 amide NH and amide carbonyl groups in the flap region.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, biological evaluation and X-ray structural studies of HIV-1 protease inhibitors containing substituted fused-tetrahydropyranyl tetrahydrofuran as P2-ligands

et al. 2015

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“…Reactions were performed in flame-dried glassware under an atmosphere of N2 unless otherwise noted. Compounds 7 4a , 14 16 , and 15 17 were prepared by literature procedures.…”

Section: Resultsmentioning

confidence: 99%

“…Construction of dihydropyran 4 was envisioned by means of a Lewis acid catalyzed diene-aldehyde cyclocondensation reaction 15 . To this end, 2(S)benzyloxypropanal (14) was prepared from (S)-ethyl lactate (6) in two steps, 73% overall yield, by the literature procedure 16 . Reaction of 14 with 1methoxy-2-methyl-3-(trimethylsiloxy)-1,3-butadiene (15) 17 in the presence of BF3•Et2O, followed by work-up with trifluoroacetic acid gave an inseparable mixture of diastereomeric dihydropyrones 16 and 17 in a 1.6:1 ratio (Scheme 4).…”

Section: Scheme 3 Epimerization Of Trans-12 To Cis-3mentioning

confidence: 99%

Synthetic Studies of Ambruticin: Preparation of the C1-C8 Tetrahydropyran and the C17-C24 Dihydropyran Segments

Liu¹,

Wondergem²,

Donaldson³

2015

Mediterr.J.Chem

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“…We have also looked into the enantioselective reduction of 1,2-dicarbonyl compounds. We were faced with the problem of the reduction of ␣hydroxyketones in the total synthesis of descarestrictine (published recently [13]) (Scheme 10).…”

Section: Methodsmentioning

confidence: 99%

Applications of chiral sulfoxides in enantioselective synthesis of diols and total synthesis of natural products

Solladié

2002

Heteroatom Chemistry

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In 1977 we published the first asymmetric aldoltype condensation of ␣-sulfinyl ester enolates giving ␤-hydroxy esters with a high enantioselectivity (ee > 85%) [1]. Since that time the use of chiral sulfoxides in asymmetric synthesis has been widely developed [2]. One of the most useful results that we obtained later concerns the reduction of ␤-ketosulfoxides [3] (Scheme 1). ␤-Ketosulfoxides are readily prepared from esters and their reduction with diisobutylaluminum (DIBAL) and ZnCl 2 /DIBAL gives an opposite diastereoselectivity higher than 95%. By desulfurization, it is possible to transform ␤-hydroxysulfoxides into the corresponding enantiomerically pure carbinols.Most of the experimental results show that chelated species and intramolecular hydride transfers are important factors for the control of the diastereoselectivity [3,4]. This efficient asymmetric synthesis of methylcarbinols has been used in macrolide synthesis; for example, in the case of Lasiodiplodin [5] (Scheme 2), it was possible to prepare the seco-ester in the very last step of the synthesis in either of the two possible configurations via the corresponding ␤-ketosulfoxide.In this short review we cover only the formation of enantiomerically pure diols. Of course, from the preceding results, it follows that C 2 symmetric diols can be prepared in enantiomerically pure form by reduction of diketodisulfoxides [6], obtained for example from methyl succinate and (R)-methyl ptolylsulfoxide (Scheme 3). This finding can be extended to the asymmetric synthesis of spiro ketals [7] (Scheme 4). In the case of 6-membered spiro ketals [7a], the configuration of the spiro center was controlled during the cyclization by the anomeric effect. The sulfinyl groups can be easily transformed into the two methyl groups present in natural products by desulfurization with Raney Nickel.In a sharp contrast to the case of 5-membered spiro-ketals [7b] (Scheme 5), the configuration of the chiral spiro-center was not controlled by the anomeric effect. The cyclization of the corresponding dihydroxy-disulfoxide under classical conditions (PPTS, acetone) afforded indeed a 1:1 mixture of 443

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Enantioselective Synthesis of (+)-(2R,3S,6R)-Decarestrictine L

Cited by 24 publications

References 34 publications

Design, synthesis, biological evaluation and X-ray structural studies of HIV-1 protease inhibitors containing substituted fused-tetrahydropyranyl tetrahydrofuran as P2-ligands

Design, synthesis, biological evaluation and X-ray structural studies of HIV-1 protease inhibitors containing substituted fused-tetrahydropyranyl tetrahydrofuran as P2-ligands

Synthetic Studies of Ambruticin: Preparation of the C1-C8 Tetrahydropyran and the C17-C24 Dihydropyran Segments

Applications of chiral sulfoxides in enantioselective synthesis of diols and total synthesis of natural products

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