Catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters:: Application to 1,3-polyol/α-pyrone natural product synthesis

被引：57

作者：

Tosaki, SY ^{[1
]}

Nemoto, T ^{[1
]}

Ohshima, T ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol0273708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We describe a catalytic asymmetric synthesis of both syn. and anti-3,5-dihydroxy esters. The method relies upon catalytic asymmetric epoxidation of alpha,beta-unsaturated imidazolides and amides, using lanthanide-BINOL complexes, and diastereoselective reduction of ketones. The method was applied to the enantioselective syntheses of 1,3-polyol/alpha-pyrone natural products 9a, 9b, and strictifolione (10). The absolute stereochemistry of 9a and 9b was also determined.

引用

页码：495 / 498

页数：4

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