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Paper | Special issue | Vol 47, No. 1, 1998, pp.439-451
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)67
Asymmetric Synthesis of Thietanose

Jun'ichi Uenishi,* Mitsuhiro Motoyama, Yumi Kimura, and Osamu Yonemitsu

*Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Okayama 700-0005, Japan

Abstract

Syntheses of optically active thietanose, (2R,3R,4R)-4-acetoxymethyl-3-(tert-butyldimethylsilyl)oxy-2-ethoxythietane (6) and (2R,3R,4R)-3-(tert-butyldimethylsilyl)oxy-4-[(tert-butyldimethylsilyl)oxy]methyl-2-ethoxythietane (23) are described. The key intermediate, (2S,3S)-4,4-bis(ethoxy)-3-(tert-butyldimethylsilyl)oxy-1,2-epithiobutane (7) has been derived from (Z)-2-butene-1,4-diol in 13 steps. Although direct transformation of 7 to thietanose (6) failed, regio and stereospecific ring opening of the episulfide ring in 7 and acid catalyzed cyclization of the resulting 3-mercaptobutanal diethyl acetal (20) was successful in forming of a thietane ring to give 6. The structure of 6 and 23 was confirmed by spectroscopic analyses including NOE experiments.