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Paper | Regular issue | Vol 43, No. 1, 1996, pp.113-126
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7232
Asymmetric Synthesis of (+)- and (-)-Eptazocine via an Enzymatic Reaction

Shunsaku Shiotani*, Hirohiko Okada, Takako Yamamoto, Kumiko Nakamata, Jun Adachi, and Hiromasa Nakamoto

*Department of Chemistry, Faculty of Science, Toyama University, Gofuku 3190, Toyama 930, Japan

Abstract

Starting from (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (R-(+)-4) prepared by enzymatic monoacetylation of 2-(p-methoxybenzyl)propane-1,3-diol (3) with lipase PS in the presence of vinyl acetate as an acetyl donor, lactones ((+)- and (-)-6) were obtained. Using the lactones, (+)- and (-)-eptazocine were synthesized.