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Synthesis of the mitomycin and FR900482 ring systems via dimethyldioxirane oxidation
Vincent J Colandrea1, Shanthi Rajaraman, Leslie S Jimenez
1Department of Chemistry & Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854-8087, USA.
Organic Letters
|March 14, 2003
Abstract:
[reaction: see text] Dimethyldioxirane 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.