Synthesis of four-membered ring spiro-β-lactams by epoxide ring-opening

被引：13

作者：

Benfatti, Fides ^{[1
]}

Cardillo, Giuliana ^{[1
]}

Gentilucci, Luca ^{[1
]}

Tolomelli, Alessandra ^{[1
]}

机构：

[1] Univ Bologna, Dipartmento Chim, I-40126 Bologna, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 19期

关键词：

lactams; oxygen heterocycles; spiro compounds; ring-opening; regio selectivity; HUMAN CYTOMEGALOVIRUS PROTEASE; 3,4-DISUBSTITUTED AZETIDINONES; STEREOSELECTIVE-SYNTHESIS; SELECTIVE INHIBITORS; ASYMMETRIC-SYNTHESIS; SERINE-PROTEASE; LEWIS-ACIDS; CATHEPSIN-K; TRANSPOSITION; MONOBACTAMS;

D O I：

10.1002/ejoc.200601110

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of hydroxy epoxides have been obtained from well defined hydroxy-alkenyl derivatives. Their subsequent intramolecular ring-opening allowed unprecedented classes of spiro-lactams to be obtained. The effect of the epoxide stereochemistry and of the reaction temperature on the regioselective formation of five- or four-membered ring spiro derivatives was explored. This transformation is part of a program directed towards the synthesis of polyfunctionalized beta-lactams as cholesterol absorption inhibitors (CAIs).

引用

页码：3199 / 3205

页数：7

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