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Synlett 1997; 1997(SI): 515-517
DOI: 10.1055/s-1997-6110
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Asymmetric Synthesis of the CBI Alkylation Subunit of the CC-1065 and Duocarmycin Analogs

Dale L. Boger* , Jeffrey A. McKie, Christopher W. Boyce
  • *Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
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Publication Date:
31 December 2000 (online)

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Two exceptionally short and effective asymmetric syntheses of N-BOC-CBI are detailed based on an asymmetric hydroboration (80% ee) or Jacobsen epoxidation (92% ee) of a 3,4-dihydrobenzo[f]quinoline followed by direct, transannular spirocyclization for introduction of the activated cyclopropane.

asymmetric hydroboration - Jacobsen epoxidation - CC-1065 - duocarmycins - transannular Ar-3' alkylation