Chelation-controlled reduction:: Stereoselective formation of syn-1,3-diols and synthesis of compactin and mevinolin lactone

被引：37

作者：

Ghosh, AK ^{[1
]}

Lei, H ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 25期

关键词：

D O I：

10.1021/jo020402k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chelation-controlled reduction of chiral beta-alkoxy ketones containing a competing beta'-oxygen functionality has been investigated. Various syn-1,3-diols were prepared conveniently by reduction of beta-alkoxy ketones with LiI/LiAlH4 (syn:anti selectivity up to > 99: 1). The corresponding beta-alkoxy ketones were derived from nitro-aldol reactions of chiral alkoxy aldehydes with a series of nitro compounds. This methodology is utilized in a short and efficient synthesis of the delta-lactone moiety of the HMG-CoA reductase inhibitors compactin and mevinolin.

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页码：8783 / 8788

页数：6

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