CATALYTIC, ASYMMETRIC-SYNTHESIS OF THE CARBACEPHEM FRAMEWORK

被引：49

作者：

GUZZO, PR ^{[1
]}

MILLER, MJ ^{[1
]}

机构：

[1] UNIV NOTRE DAME,DEPT CHEM & BIOCHEM,NOTRE DAME,IN 46556

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 17期

关键词：

D O I：

10.1021/jo00096a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic, asymmetric synthesis of the carbacephem beta-lactam framework is reported. The initial asymmetric center was established by catalytic hydrogenation of beta-keto ester 12 with (S)-Ru-BINAP. The beta-lactam ring was prepared using the hydroxamate approach (14 --> 15). The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 --> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 --> 25).

引用

页码：4862 / 4867

页数：6

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