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Total synthesis of thienamycin analogs. II Synthesis of 2-alkyl and 2-aryl thienamycin nuclei

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
21
Issue
21
Identifiers
DOI: 10.1016/s0040-4039(00)71473-0

Abstract

Abstract A new general synthesis leading to 2-alkyl and 2-aryl-1-carba-2-penem-3-carboxylic acids involves the preparation of a key thiolester intermediate 3. This is reacted with Me 2CuLi or (C 6H 5) 2MgCuX to give the corresponding methyl or phenyl ketone which undergoes a Wittig reaction to give the desired penems, which can be deblocked photolytically or by hydrogenolysis to give acids with good antibacterial activity.

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