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Microbial transformation of precocene II: oxidative reactions by Streptomyces griseus
F S Sariaslani1, L R McGee, D W Ovenall
1Central Research and Development Department, E. I. du Pont de Nemours and Company, Wilmington, Delaware 19898.
Abstract:
Various species of "Streptomyces," "Aspergillus," "Rhodotorula," "Brevilegnia," "Syncephalastrum," and "Stysanus" were found to transform precocene II to three major metabolites. These major biotransformation products were isolated from a preparative-scale incubation of precocene II with Streptomyces griseus and were conclusively identified as (-)cis- and (+)trans-precocene II-3,4-dihydrodiols and (+)-3-chromenol. 18O2 incorporation studies indicated the involvement of a monooxygenase enzyme system in precocene II transformation by S. griseus. A mechanism is proposed for the formation of (+)-3-chromenol.