(+)-Cystothiazole G: isolation and structural elucidation |
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Authors: | Hiroyuki Akita Takamitsu Sasaki Yoshihiro Suzuki Youji Sakagami Ryosuke Fudou |
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Institution: | a School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan b Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan c Institute of Life Science, Ajinomoto Co. Inc., Kawasaki-ku, Kawasaki 210-8681, Japan |
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Abstract: | Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpent-4-yne-1,2-diol (6) derived from (2R,3S)-epoxybutanoate 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 the (+)-cystothiazole G (2), whose spectral data were identical with those of the natural product (+)-2. Thus, the stereochemistry of cystothiazole G (2) was proved to be (4R,5S,6(E)). |
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Keywords: | (+)-Cystothiazole G Cyclization-methoxycarbonylation Chiral synthesis |
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