Stereopentads Derived from a Sequence of Mukaiyama Aldolization and Free Radical Reduction on α-Methyl-β-alkoxy Aldehydes: A General Strategy for Efficient Polypropionate Synthesis

被引：25

作者：

Brazeau, Jean-Francois

Mochrian, Philippe

Prevost, Michel

Guindon, Yvan ^{[1
]}

机构：

[1] Inst Rech Clin Montreal, Bioorgan Chem Lab, Montreal, PQ H2W 1R7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 01期

基金：

加拿大自然科学与工程研究理事会;

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; HYDROGEN-TRANSFER REACTIONS; IN-SITU DERIVATIZATION; ALDOL REACTIONS; CROTYLATION REACTIONS; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE MUKAIYAMA; STEREOCONTROLLED SYNTHESIS; ENHANCE STEREOSELECTIVITY; POLYKETIDE SYNTHESIS;

D O I：

10.1021/jo8021583

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In a stereodivergent manner, all 16 diastereomeric stereopentads 7-22 were synthesized starting with alpha-methyl-beta-alkoxy aldehydes 25 and 27. We designed an approach based on a sequence of a Mukaiyama aldolization with enoxysilane 24 followed by a hydrogen transfer reaction. Recent advancements concerning these reactions are described, and novel key intermediates are characterized in the aldol step. The synthesis of C(1)-C(1) fragement 60 of zincophorin, which contains a synthetically challenging stereopentad unit, is described attesting the usefulness of our strategy.

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收藏

页码：64 / 74

页数：11

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