Journal of the American Chemical Society p. 9318 - 9327 (1992)
Update date:2022-08-05
Topics:
Boger, Dale L.
Palanki, Moorthy S.S.
A concise and effective nine to ten step synthesis of 9a-(chloromethyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (C2BI) is detailed based on the implementation of a key 5-exo-trig aryl radical-alkene cyclization for direct introduction of a selectively protected 3,3-bis(hydroxymethyl)indoline. The incorporation of C2BI into functional analogs of CC-1065 and the duocarmycins (C2BI-COPI1, C2BI-CDPI2, C2BI-TMI, and C2BI-indole2) is described. The fundamental solvolytic behavior of N-BOC-C2BI is detailed (t1/2 = 433 h, pH = 3) in studies which reveal that the agent is approximately 12 times more stable than the authentic alkylation subunit of CC-1065 and that it participates in the stereoelectronically-controlled reaction with nucleophilic addition to the least substituted cyclopropane carbon. Preliminary studies demonstrating the DNA alkylation and cross-linking properties of C2BI-CDPI2 are presented.
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