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Communication | Regular issue | Vol 36, No. 7, 1993, pp.1489-1492
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6374
Synthesis of (-)-Nonactic Acid: Application of γ-Dithio-β-hydroxy Ester Prepared by Microbial Reduction as a Chiral Building Block

Kazuhiko Takatori, Nobuyuki Tanaka, Kenji Tanaka, and Masahiro Kajiwara*

*Department of Medicinal Chemistry, Meiji College of Pharmacy, 1-22-1 Yato-cho, Tanashi-shi, Tokyo 188, Japan

Abstract

A γ-dithio-β-hydroxy ester (2), prepared by microbial reduction with baker’s yeast, was used as a chiral building block, for the synthesis of (-)-nonactic acid (1). It was converted to the lithium acetylide via 5, of which 1,2-addition to the aldehyde (6) followed by reduction gave the 3-silyloxy-6-tosyloxynonane (8b). On cleavage of the silyl ether, cyclization proceeded with complete inversion of configuration at C-6 to afford a cis-2,5-disubstituted tetrahydrofuran (9), which was led to 1.