Formal total syntheses of the beta-lactam antibiotics thienamycin and PS-5

被引：56

作者：

Jacobi, PA

Murphree, S

Rupprecht, F

Zheng, WJ

机构：

[1] Hall-Atwater Laboratories, Wesleyan University, Middletown

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 07期

关键词：

D O I：

10.1021/jo952092u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral nonracemic acetylenic acids of general structure 11, prepared using the Schreiber modification of the Nicholas reaction, have been converted to beta-amino acid derivatives of type 12 by a two-step sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 12 are excellent precursors for beta-lactams of the carbapenem class, including the important antibiotics thienamycin (1) and PS-5 (4).

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页码：2413 / 2427

页数：15

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