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

✍ Scribed by L. Cama; B.G. Christensen

Publisher: Elsevier Science
Year: 1980
Tongue: French
Weight: 225 KB
Volume: 21
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)71473-0

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✦ Synopsis

Jersey 07065

A new general synthesis leading to 24kyl and 2-aryl-l-carba-2-penem-3-carboxylic acids involves the preparation of a key thiolester intermediate 3. This is reacted with Me CuLi or (C6H5)2MgCuX to give the correspond@ methyl or phenyl ketone which undergoes a Wittig rea A* mn to give the desired penems, which can be &blocked photolytically or by hydrogenolysis to give acids with good antibacterial activity.

Recently we reported' the total synthesis of the thienamycin nucleus 6 (R=H), involving a Wittig reaction for ring closure. We now wish to report an extension of this synthesis, which provides a general method for synthesizing 2-substituted l-carba-Zpenems.

The synthesis involves the preparation of ketone intermediate 4 v& the reaction of easily available lithium or magnesium aryl or alkyl cuprate on a

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