| Abstract
| - A short, asymmetric synthesis of the 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI)analogue of the CC-1065 and duocarmycin alkylation subunits is detailed that employs an effectiveenzymatic desymmetrization reaction of prochiral diol 12 using a commercially available Pseudomonas sp. lipase. The optically active monoacetate (S)-13 is furnished in exceptional conversions(88%) and optical purity (99% ee) and serves as an intermediate for the preparation of eitherenantiomer of CBI. Similarly, the Pseudomonas sp. lipase resolved the racemic intermediate 19,affording advanced intermediates of CBI in good conversions and optical purity (99% ee), andprovided an alternative approach to the preparation of optically active CBI derivatives.
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