TOTAL SYNTHESES OF PENICILLANIC ACID S,S-DIOXIDE AND 6-AMINOPENICILLANIC ACID USING (BENZYLOXY)NITROMETHANE

被引：35

作者：

BARRETT, AGM

SAKADARAT, S

机构：

[1] Department of Chemistry, Northwestern University, Evanston

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 17期

关键词：

D O I：

10.1021/jo00304a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereocontrolled total syntheses of penicillanic acid S,S-dioxide (10) and 6-aminopenicillanic acid (26) from (S)-aspartic acid and (r,R)-tartaric acid, respectively, are described. The key steps involve the preparation and cyclization of the nitroalkenes 8 and 23. Reaction of 8 and 23 with tetrabutylammonium fluoride followed by ozone and DBU gave the bicyclic 0-lactams 9 and 24. These substances were readily transformed into the target penicillanic acid derivatives 10 and 26. © 1990, American Chemical Society. All rights reserved.

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页码：5110 / 5117

页数：8

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