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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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