Journal
CHEMICAL COMMUNICATIONS
Volume -, Issue 4, Pages 385-400Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b814375g
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Funding
- Center for Green Photo-Science and Technology
- Ministry of Education, Science, Sports and Culture, Japan
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The first asymmetric total syntheses of botcinins C (18), D (19), E (20), and F (21), botcinic acid (22), botcinic acid methyl ester (23), botcineric acid (26), and 3-O-acetylbotcinic acid methyl ester (27) were achieved. The structures of these compounds have been unequivocally determined through their total syntheses and those of 20, 22, 23, 26, and 27 are identified with the revised forms of the natural products formerly assumed to be 2-epibotcinolide (10), botcinolide (6), 4-O-methylbotcinolide (7), homobotcinolide (11), and 3-O-acetyl-5-O-methylbotcinolide (8), respectively. It was further proved that the proposed nine-membered ring structure of 2-epibotcinolide (10) is very unstable and the ineluctable translactonization easily occurred to form the corresponding gamma-lactone 57.
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