Stereoselective synthesis of precursors of the macrolide antibiotics via reactions of sulfur ylides with chiral aldehydes

被引：14

作者：

López-Herrera, FJ ^{[1
]}

Sarabia-García, F ^{[1
]}

Pedraza-Cebrián, GM ^{[1
]}

Pino-González, MS ^{[1
]}

机构：

[1] Univ Malaga, Fac Ciencias, Dept Bioquim Biol Mol & Quim Organ, E-29071 Malaga, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 07期

关键词：

macrolide antibiotics; sulphur ylides; epoxides;

D O I：

10.1016/S0040-4039(98)02613-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of stabilized sulfur ylides with chiral aldehydes provided epoxides with high stereoselectivity. The opening of the resulting epoxides with lithium dimethyl cuprate gave 2-methyl-3-hydroxy amides which represent potentially useful building blocks for the synthesis of macrolide natural products. These amides were transformed into chiral aldehydes, with a methyl group in the alpha-position, and were reacted, in a iterative process, with a sulfur ylide reagent to give, in high yield and stereoselectivity, the epoxides with the stereochemistry according to Felkin-Ahn control. Finally, opening of the epoxide with the Oilman reagent provided a compound with four stereocenters occurring in the macrolide-type of natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1379 / 1380

页数：2

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