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Issue 4, 2009
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Chemistry and structural determination of botcinolides, botcinins, and botcinic acids

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Abstract

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 γ-lactone57.

Graphical abstract: Chemistry and structural determination of botcinolides, botcinins, and botcinic acids

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Publication details

The article was received on 18 Aug 2008, accepted on 03 Oct 2008 and first published on 03 Dec 2008


Article type: Feature Article
DOI: 10.1039/B814375G
Citation: Chem. Commun., 2009,0, 385-400

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

    I. Shiina and H. Fukui, Chem. Commun., 2009, 0, 385
    DOI: 10.1039/B814375G

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