Synlett 2003(8): 1149-1150
DOI: 10.1055/s-2003-39910
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Sung Ho Kang*, Mihyong Kim, Do Hyun Ryu
Center for Molecular Design and Synthesis, Department of Chemistry, School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology, Daejeon 305-701, Korea
Fax: +82(42)8692810; e-Mail: [email protected];
Further Information

Publication History

Received 14 April 2003
Publication Date:
11 June 2003 (online)

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.

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