SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .1. FACILE SYNTHESIS OF A KEY INTERMEDIATE - 4-ACETOXY-3-(1-HYDROXYETHYL)-2-AZETIDINONE

被引：0

作者：

SUNAGAWA, M ^{[1
]}

MATSUMURA, H ^{[1
]}

ENOMOTO, M ^{[1
]}

INOUE, T ^{[1
]}

SASAKI, A ^{[1
]}

机构：

[1] SUMITOMO PHARMACEUT CO LTD, RES LABS, 3-1-98 KASUGADE NAKA, KONOHANA KU, OSAKA 554, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1991年 / 39卷 / 08期

关键词：

PENEM; CARBAPENEM; (R)-1-HYDROXYETHYL GROUP; (3R; 4R)-4-ACETOXY-3-[(R)-1-HYDROXYETHYL]-2-AZETIDINONE; (2+2) CYCLOADDITION; OXYMERCURATION-REDUCTION; OXIDATIVE DECARBOXYLATION;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A highly efficient synthesis of (3R,4R)4-acetoxy-3-[(R)-1-hydroxyethyl]-2-azetidinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, was accomplished. It was found that oxymercuration-reduction of easily obtainable 4-alkyloxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone could be employed as a key stereoselective reaction. The chiral starting material was obtained by optical resolution or asymmetric (2 + 2) cycloaddition. The desired product was afforded in four steps, that is, oxymercuration-reduction, oxidative decarboxylation, protection of the hydroxy group and removal of the N-protecting group.

引用

页码：1931 / 1938

页数：8

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