Determination of the absolute structure of (+)-cystothiazole B |
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Authors: | Sasaki Takamitsu Kato Keisuke Akita Hiroyuki |
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Affiliation: | School of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan. |
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Abstract: | Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpenta-4-yne-1,2-diol (6) derived from (2R,3S)-epoxy butanoate 5, followed by methylation, gave the tetrahydro-2-furylidene acetate (-)-7, which was converted to the left-half aldehyde (+)-3. A Wittig reaction between (+)-3 and the phosphoranylide derived from the bithiazole-type phosphonium iodide 4 using lithium bis(trimethylsilyl)amide afforded (+)-cystothiazole B (2), the spectral data of which were identical to those of the natural product (+)-2. Thus the stereochemistry of cystothiazole B (2) was confirmed to be [4R, 5S, 6(E)]. |
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