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Paper | Regular issue | Vol 71, No. 1, 2007, pp.75-85
Published online, 17th November, 2006
DOI: 10.3987/COM-06-10907
■ Total Synthesis of (4R,5S)-Melithiazol C and (3R,4S)-Cystothiazole E

Hiroyuki Takayama, Keisuke Kato, Masayuki Kimura, and Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

A Wittig reaction between (+)-chiral aldehyde (4R,5R)-3 and the phosphoranylide derived from the mono-thiazole-type phosphonium iodide [(±)-10] using lithium bis(trimethylsilyl)amide afforded the (+)-melithiazol C (1), whose spectral data were identical with those of the natural product [(+)-1]. Moreover, the Julia’s coupling of aldehyde (21) and the bithiazole-type sulfone (5) followed by the consecutive deprotection and Dess-Martin oxidation gave the (+)-cystothiazole E (2), whose spectral data were identical with those of the natural product [(+)-2].