Abstract
The microbiological transformation of 13α,17-dihydroxy-stemodane ( 2 ) by the fungus Mucor plumbeus afforded 13α,17,19-trihydroxy-stemodane ( 3 ), 3β,13α,17-trihydroxy-stemodane ( 5 ), 3-oxo-13α,17-dihydroxy-stemodane ( 7 ), 7α,13α,17,19-tetrahydroxy-stemodane ( 8 ), 3β,11α,13α,17-tetrahydroxy-stemodane ( 10 ), 3β,7α,13α,17-tetrahydroxy-stemodane ( 12 ), 3β,8β,13α,17-tetrahydroxy-stemodane ( 14 ), 2α,13α,17-trihydroxy-stemodane ( 16 ), 2α,13α,17,19-tetrahydroxy-stemodane ( 17 ), 2α,3β,13α,17-tetrahydroxy-stemodane ( 20 ) and 3β,11β,13α,17-tetrahydroxy-stemodane ( 22 ), whilst the incubation of 13α,14-dihydroxy-stemodane ( 25 ) gave 3β,13α,14-trihydroxy-stemodane ( 28 ), 2α,13α,14-trihydroxy-stemodane ( 29 ) and 13α,14,19-trihydroxy-stemodane ( 30 ). Preference for hydroxylations of ring A at C-2(α), C-3(β) and C-19 were observed in both incubations. An interesting rearrangement of 13α,14α-dihydroxy-stemodanes to 14-oxo derivatives with an unusual carbon framework has been observed under acetylation conditions. We have named this skeleton prestemodane, which, as a hydrocarbon ion, had been postulated as a biogenetic precursor of stemodane.
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