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Communication | Regular issue | Vol 38, No. 2, 1994, pp.277-280
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6603
Versatile Synthesis of an Intermediate for the 1β-Methylcarbapenem Synthesis

Koichi Hirai,* Yuji Iwano, Isamu Mikoshiba, Hiroo Koyama, and Takahide Nishi

*New Lead Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan


A 1β-methylcarboxylate (1) which is a requisite intermediate for the synthesis of the 1β-methylcarbapenem was obtained in an efficient manner by the coupling reaction of a Z(O)-pyridylthiosilyl enol ether and a 4-acetoxyazetidinone derivative in the presence of ZnCl2 in CH2Cl2. The reactive silyl enol ether was prepared by the reverse addition method in high yield.