A Stereoselective Synthesis of a Key Intermediate to 1β-Methylcarbapenem via Aziridine Ring-opening Reaction

Abstract

A stereocontrolled synthesis of azetidinone 3 as a key intermediate to 1β-methylcarbapenem 2 has been achieved via iodoamidation of trichloroacetimidate prepared from (Z)-olefinic allylic alcohol 6, aziridine ring-opening reaction with cyanide nucleophile and a tandem β-lactam formation.

Key words

stereoselective synthesis - 1β-methylcarbapenem - iodoamidation - aziridine ring-opening - tandem β-lactam formation

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