Biosynthetic Studies on the Botcinolide Skeleton:  New Hydroxylated Lactones from Botrytis c inerea

The biosynthetic origin of the botcinolide skeleton was investigated by means of feeding 13C- and 2H-labeled precursors to Botrytis cinerea. Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered lactone (7), were is...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-01, Vol.71 (2), p.562-565
Main Authors: Reino, José L, Durán-Patrón, Rosa M, Daoubi, Mourad, Collado, Isidro G, Hernández-Galán, Rosario
Format: Article
Language:English
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Summary:The biosynthetic origin of the botcinolide skeleton was investigated by means of feeding 13C- and 2H-labeled precursors to Botrytis cinerea. Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered lactone (7), were isolated. Their structures were elucidated on the basis of spectroscopic data, including one-bond and long-range 1H−13C correlations. The relative stereochemistries were determined by combined analyses of NOE data and 1H−1H coupling constants. According to the results of feeding experiments with 13C- and 2H-labeled acetate and l-S-methylmethionine, 5 is an acetate-derived polyketide whose methyl groups originate from l-S-methylmethionine. This is a rare example of the incorporation of a methyl from methionine into a supposed C3 starter unit of the polyketide synthesis.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051993s