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...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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American Chemical Society (ACS)
2020
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| Online Access: | https://hdl.handle.net/1721.1/125882 |
| _version_ | 1826189693271670784 |
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| author | Antropow, Alyssa Hope Garcia, Nicholas R. White, Kolby L. Movassaghi, Mohammad |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Antropow, Alyssa Hope Garcia, Nicholas R. White, Kolby L. Movassaghi, Mohammad |
| author_sort | Antropow, Alyssa Hope |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T08:19:59Z |
| format | Article |
| id | mit-1721.1/125882 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T08:19:59Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1258822022-09-23T12:22:31Z Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation Antropow, Alyssa Hope Garcia, Nicholas R. White, Kolby L. Movassaghi, Mohammad Massachusetts Institute of Technology. Department of Chemistry Physical and Theoretical Chemistry Organic Chemistry Biochemistry 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) 2020-06-19T14:39:12Z 2020-06-19T14:39:12Z 2018-06 2018-05 2019-12-27T19:56:04Z Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 https://hdl.handle.net/1721.1/125882 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) en 10.1021/acs.orglett.8b01428 Organic Letters 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. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Physical and Theoretical Chemistry Organic Chemistry Biochemistry Antropow, Alyssa Hope Garcia, Nicholas R. White, Kolby L. Movassaghi, Mohammad Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation |
| title | Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation |
| title_full | Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation |
| title_fullStr | Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation |
| title_full_unstemmed | Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation |
| title_short | Enantioselective synthesis of (-)-vallesine: late-stage C17-oxidation via complex indole boronation |
| title_sort | enantioselective synthesis of vallesine late stage c17 oxidation via complex indole boronation |
| topic | Physical and Theoretical Chemistry Organic Chemistry Biochemistry |
| url | https://hdl.handle.net/1721.1/125882 |
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