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Note | Regular issue | Vol 71, No. 5, 2007, pp.1203-1209
Published online, 29th March, 2007
DOI: 10.3987/COM-07-11032
Synthesis of a Diastereomeric Mixture of (4R,5S,6E,14R)- and (4R,5S,6E,14S)-Melithiazols G

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 (+)-3 and the phosphoranylide derived from the bithiazole-type phosphonium iodide [(±)-4] using lithium bis(trimethylsilyl)amide afforded a diastereomeric mixture of the (+)-(4R,5S,6E,14R)- and (4R,5S,6E,14S)-melithiazols G (1), whose NMR spectral data were identical with those of the natural product (1). The antifungal activity of the synthetic diastereomeric mixture of melithiazols G (1) against the phytopathogenic fungus, Phytophthora capsici, was evaluated by using a paper disc assay method.