HIGH PI-FACE SELECTIVITY IN ANTI-ALDOL REACTIONS OF E-ENOL BORINATES FROM CHIRAL ALKOXYMETHYL KETONES - STEREOCONTROLLED SYNTHESIS OF A C24-C32 POLYOL SUBUNIT OF RAPAMYCIN

被引：56

作者：

PATERSON, I

TILLYER, RD

机构：

[1] University Chemical Laboratory, Cambridge CB2 1EW, Lensfield Road

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 16期

关键词：

D O I：

10.1021/jo00068a002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using (c-C6H11)2BCl/Et3N, the aldol reactions of the alpha-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95% yield with greater-than-or-equal-to 95% diastereoselectivity. This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of, rapamycin (10).

引用

页码：4182 / 4184

页数：3

共 43 条

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