Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation

Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation

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 a...

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Bibliographic Details
Main Authors: Antropow, Alyssa Hope (Author), Garcia, Nicholas R. (Author), White, Kolby L. (Author), Movassaghi, Mohammad (Author)
Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
Format: Article
Language:English
Published: American Chemical Society (ACS), 2020-06-19T14:39:12Z.
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Summary: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.
NIH-NIGMS (grant no. GM074825)

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