Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer

Koukal, Petr; Kotora, Martin

doi:10.1002/ejoc.201701416

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Cited by 3 publications

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“…As per our retrosynthetic plan for goniobutenolide A and B, our synthetic journey commenced from known enantiopure aldehyde 17 32 synthesized from ( R )-mandelic acid (see the ESI† for experimental details). Lithium TMS-acetylide addition to the aldehyde 17 produced a 10 : 1 diastereomeric mixture of compounds 20 and 21 .…”

Section: Resultsmentioning

confidence: 99%

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

et al. 2022

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Biocatalytic stereoselective synthesis of methyl mandelates by engineering a cytochrome P450 hydroxylase

Xie

Zhang

et al. 2024

Green Synthesis and Catalysis

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A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands

et al. 2021

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A general procedure for the asymmetric synthesis of highly substituted 1,2-amino alcohols in high yield and diastereoselectivity is described that uses organometallic additions of a wide range of nucleophiles to tertbutylsulfinimines as the key step. The addition of organolithium reagents to these imines follows a modified Davis model. The diastereoselectivity for this reaction depends significantly on both the nucleophile and electrophile. These highly substituted 1,2-amino alcohols are used to synthesize stereochemically diverse and structurally novel, polysubstituted 2,2′-methylene(bisoxazoline) ligands in high yields.

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Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer

Abstract: Abstract:The key aetheramide A intermediate with the natural (R,R,R) configuration along with the one having the unnatural (R,S,R) configuration was synthesized. The synthesis of both stereoisomers was accomplished by Suzuki coupling of two ad-

Cited by 3 publications

References 26 publications

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

Biocatalytic stereoselective synthesis of methyl mandelates by engineering a cytochrome P450 hydroxylase

A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands

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