ol026738y_si_001.pdf (28.87 kB)
Synthesis of the Mitomycin and FR900482 Ring Systems via Dimethyldioxirane Oxidation
journal contribution
posted on 2003-02-25, 00:00 authored by Vincent J. Colandrea, Shanthi Rajaraman, Leslie S. JimenezDimethyldioxirane oxidizes a 2,3-dihydo-1H-pyrrolo[1,2-a]indole unsubstituted at the C-9 position stereoselectively to form a hydroxy ketone
with all the basic elements of the mitomycin ring system. On the other hand, a 2,3-dihydo-1H-pyrrolo[1,2-a]indole derivative substituted with
an alkyl group at C-9 undergoes an oxidative ring expansion in the presence of dimethyldioxirane to give an FR900482 analogue.