Tetrahedron

Total synthesis of a novel 2-thiabicyclo [3.2. 0] heptan-6-one analogue of penicillin N

AC Ferguson, RM Adlington, DH Martyres, PJ Rutledge…

Index: Ferguson, Amanda C.; Adlington, Robert M.; Martyres, Domnic H.; Rutledge, Peter J.; Cowley, Andrew; Baldwin, Jack E. Tetrahedron, 2003 , vol. 59, # 41 p. 8233 - 8243

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Citation Number: 21

Abstract

A route has been developed which allows synthesis of novel cyclobutanone analogues of penicillin. This is illustrated by the synthesis of (1R, 4R, 5R, 5′ R, 7S)-(1b) and (1S, 4S, 5S, 5′ R, 7R)-7-[5′-amino-5′-carboxy] pentanamido]-2-thiabicyclo [3.2. 0] heptan-6-one-4- carboxylate (1a), an analogue of penicillin N. The key steps in the synthesis were the formation of the bicyclic structure via a [2+ 2] cycloaddition and the introduction of nitrogen ...