Biotransformation of Humulene by Fungi and Enantioselectivity of the Strains Used

Abstract

Abstract Humulene was transform ed by strains of Chaetomium cochlioides and Diplodia gossypina ATCC 10936 affording 33 new humulanes. The first step is a non-enantioselective epoxidation of the 1,2-double bond, whereas the subsequent hydroxylations were performed preferably at the 1R ,2R -epoxide. To proof these results the anti-1,2;8,9-diepoxide was synthesized and used as substrate. While the 1R ,2R ,8S,9S-antipode of this diepoxide was hydroxylated the other one was recovered unchanged. Diplodia gossypina ATCC 10936 gave the same products but differing in relative and absolute configurations.