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

Author(s)
Antropow, Alyssa Hope; Garcia, Nicholas R.; White, Kolby L.; Movassaghi, Mohammad
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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.
Date issued
2018-06
URI
https://hdl.handle.net/1721.1/125882
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Antropow, Alyssa H., et al., "Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation." Organic Letters 20, 12 (2018): p. 3647-50 doi 10.1021/acs.orglett.8b01428 ©2018 Author(s)
Version: Author's final manuscript
ISSN
1523-7060
1523-7052
Keywords
Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry

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