Anomalous Microbial Transformations on the Taxane Ring of 10-DAB by a Strain of the Fungus Curvularia lunata: Transbenzoylation, Transacetylation, and Opening of the Oxetane Ring

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• 作者：Alberto Arnone ; Adriana Bava ; Giovanni Fronza ; Gianluca Nasini
• 刊名：Journal of Natural Products
• 出版年：2009
• 出版时间：November 30, 2009
• 年：2009
• 卷：72
• 期：11
• 页码：2000-2004
• 全文大小：140K
• 年卷期：v.72,no.11(November 30, 2009)
• ISSN：1520-6025

文摘

The fermentation of 10-deacetylbaccatin III (10-DAB) (1) with Curvularia lunata afforded the taxane hemiacetals 2a and 3, characterized by extensive structural modification, including C-2 to C-1 transbenzoylation, oxidation of the C-2 hydroxyl, formation of a C-9/C13 hemiacetal, epimerization at C-10, and migration of the endocyclic double bond to an exocyclic location. In compound 3, an acetate-assisted opening of the oxetane ring was also observed.