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Biotransformation of the diterpene ribenone by Mucor plumbeus

AuthorsFraga, Braulio M. ; Hernández, Melchor G.; González, Pedro; López, Matías; Suárez, Sergio
KeywordsMicrobial reactions
X-ray crystal structures
Terpenes and terpenoids
Issue Date2001
CitationTetrahedron 57: pp. 761-770 (2001)
AbstractThe microbiological transformation of the diterpene ribenone (3-oxo-ent-13-epi-manoyl oxide) by the fungus Mucor plumbeus has been studied. Epoxidation of the vinyl group constitutes the main reaction and there exists a preference for hydroxylation at C-1(a), C-6(a or B) and C-12(B) and, to a lesser degree, at C-7(a) and C-11(B). Other observed reactions were the reduction of the 3-oxo group to a 3B-alcohol and the formation of metabolites with a 1,2-double bond. In this work the stereochemistry at C-14 of the diterpenes excoecarins A, B and C has been revised on the basis of X-ray data.
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