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Communication | Regular issue | Vol 24, No. 4, 1986, pp.893-896
Published online, 1st January, 1970
DOI: 10.3987/R-1986-04-0893
1,3-peri-Repulsion; a New Synthetic Control Factor for Methyl Epimers by Opening or Closing γ-Lactone and Its Fixation by Dithioacetal

Tetsuichi Shibata,* Tamiko Ohkura, Nobuko Shimizu, and Seiichi Inayama

*Pharmaceutical Institute, School of Medicine, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan

Abstract

The inversion of methyl adjacent to ketone from equatorial to axial was achieved by virture of 1,3-peri-repulsion of the hydroxyl group formed by opening γ-lacone in a series of tetrahydro-l-α-santonin and their derivatives, and was confirmed chemically by fixation of the adjacent ketone by ethylene dithioacetal without epimerization of the methyl group.