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01354 am a22002533u 4500 |
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125882 |
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|a Antropow, Alyssa Hope
|e author
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|a Massachusetts Institute of Technology. Department of Chemistry
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|a Garcia, Nicholas R.
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|a White, Kolby L.
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|a Movassaghi, Mohammad
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|a Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation
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|b American Chemical Society (ACS),
|c 2020-06-19T14:39:12Z.
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|z Get fulltext
|u https://hdl.handle.net/1721.1/125882
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|a 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.
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|a NIH-NIGMS (grant no. GM074825)
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|a en
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|a Physical and Theoretical Chemistry
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|a Organic Chemistry
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|a Biochemistry
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|a Article
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|t 10.1021/acs.orglett.8b01428
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|t Organic Letters
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