Chemistry and structural determination of botcinolides, botcinins, and botcinic acids

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 () were achieved. The structures of these compounds have been unequivocally determined through the...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2009-01 (4), p.385-400
Main Authors: Shiina, Isamu, Fukui, Hiroki
Format: Article
Language:English
Subjects:
Decanoates - chemical synthesis
Decanoates - chemistry
Decanoates - isolation & purification
Lactones - chemical synthesis
Lactones - chemistry
Lactones - isolation & purification
Pyrones - chemical synthesis
Pyrones - chemistry
Pyrones - isolation & purification
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Summary: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 () were achieved. The structures of these compounds have been unequivocally determined through their total syntheses and those of 20, 22, 23, 26, and 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 .
ISSN:1359-7345
1364-548X
DOI:10.1039/b814375g