Total synthesis of (+)-blennolide C and (+)-gonytolide C via spirochromanone |
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Authors: | Kanna Adachi Sho Hasegawa Kazuaki Katakawa Takuya Kumamoto |
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Affiliation: | 1. Department of Synthetic Organic Chemistry, Research Institute of Pharmaceutical Sciences, Musashino University, 1-1-20 Shinmachi, Nishitokyo 202-8585, Japan;2. Department of Synthetic Organic Chemistry, Graduate School of Biomedical & Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 732-8553, Japan |
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Abstract: | We report the asymmetric total synthesis of (+)-blennolide C and (+)-gonytolide C isolated from endophytic fungi. The synthesis involved construction of a spirochromanone with a chiral quaternary carbon by the aldol reaction of o-hydroxyacetophenones and optically active α-oxygenated cyclohexenone, followed by cyclization under acidic conditions. Oxidative cleavage of the alkene moiety of the spirochromanone furnished the chromanone diester. Through treating the diester with a Lewis acid, the first total synthesis of (+)-blennolide C was achieved by deprotecting the oxygen functionality of the diester and simultaneous Dieckmann condensation. Total synthesis of (+)-gonytolide C was also achieved by lactone formation from the deprotected diester. |
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Keywords: | Total synthesis Xanthones Spirochromanones Asymmetric synthesis Enzymatic resolution |
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