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Enantioselective Synthesis of (−)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation

Author:
Antropow, Alyssa H., Garcia, Nicholas R., White, Kolby L., Movassaghi, Mohammad
Source:
Organic letters 2018 v.20 no.12 pp. 3647-3650
ISSN:
1523-7052
Subject:
alkaloids, chemical reactions, chemical structure, enantioselective synthesis, enantioselectivity, regioselectivity
Abstract:
The first enantioselective total synthesis of (−)-vallesine via a strategy that features a late-stage regioselective C17-oxidation followed by a highly stereoselective transannular cyclization is reported. The versatility of this approach is highlighted by the divergent synthesis of the archetypal alkaloid of this family, (+)-aspidospermidine, and an A-ring-oxygenated derivative, (+)-deacetylaspidospermine, the precursor to (−)-vallesine, from a common intermediate.
Agid:
6084129