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Chemical-microbiological synthesis of cryptomeridiol derivatives by Gliocladium roseum: semisynthesis of 11-hydroxyeudesmanolides

García-Granados, Aés.; Gutiérrez, Mía.C.; Parra, Aés.; Rivas, F.

Journal of Natural Products 65(7): 1011-1015

2002

ISSN/ISBN: 0163-3864
PMID: 12141862
Document Number: 544334
Biotransformations of 4alpha- and 4beta-hydroxyeudesmane derivatives by the filamentous fungus Gliocladium roseum were achieved. Hydroxylation at C-11 was the main action of this microorganism, producing new cryptomeridiol (12 and 14) and 4-epi-cryptomeridiol derivatives (6 and 7), respectively, in good yields. The biotransformation activity of G. roseum toward 4beta-hydroxyeudesmane was focused on the isopropyl moiety, but more scattered on the 4alpha-hydroxylated derivative, acting in both the "A" and "B" rings and the isopropyl group of the molecule. Semisyntheses of 11-hydroxyeudesmanolides from the isolated 11,12-dihydroxylated metabolites were also accomplished and used in assigning the stereochemistry of hydroxylation.

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