Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation
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nihms974426.pdf
Description
Accepted version
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1.69 MB
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Author(s)
Antropow, Alyssa Hope
Garcia, Nicholas R.
White, Kolby L.
Movassaghi, Mohammad
Date Issued
June 2018
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
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.
Subjects
Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.8b01428
