Synthesis of the mitomycin and FR900482 ring systems via dimethyldioxirane oxidation.
[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.
Colandrea
Vincent J
VJ
Department of Chemistry & Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854-8087, USA.
Rajaraman
Shanthi
S
Jimenez
Leslie S
LS
D007202:Indicators and Reagents; D016685:Mitomycin / Q000138:chemical synthesis* / Q000737:chemistry; D019384:Nucleic Acid Synthesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D007202:Indicators and Reagents; D019384:Nucleic Acid Synthesis Inhibitors; D010078:Oxazines; C053335:FR 900482; D016685:Mitomycin