Journal of Organic Chemistry p. 6234 - 6239 (1992)
Update date:2022-08-04
Topics:
Aristoff, Paul A.
Johnson, Paul D.
A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17).While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity.A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI.Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.
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()Doi:10.1016/S0040-4039(00)61328-X
(1992)