Total Synthesis of (−)-Himandrine
We describe the first total synthesis of (−)-himandrine, a member of the class II galbulimima alkaloids. Noteworthy features of this chemistry include a diastereoselective Diels−Alder reaction in the rapid synthesis of the tricycle ABC-ring system in an enantiomerically enriched form, the use of a f...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society
2012
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| Online Access: | http://hdl.handle.net/1721.1/71907 https://orcid.org/0000-0003-3080-1063 |
| _version_ | 1811070326116712448 |
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| author | Movassaghi, Mohammad Tjandra, Meiliana Qi, Jun |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Movassaghi, Mohammad Tjandra, Meiliana Qi, Jun |
| author_sort | Movassaghi, Mohammad |
| collection | MIT |
| description | We describe the first total synthesis of (−)-himandrine, a member of the class II galbulimima alkaloids. Noteworthy features of this chemistry include a diastereoselective Diels−Alder reaction in the rapid synthesis of the tricycle ABC-ring system in an enantiomerically enriched form, the use of a formal [3+3] annulation strategy to secure the CDE-ring system with complete diastereoselection, and successful implementation of our biogenetically inspired oxidative spirocyclization of an advanced intermediate. The successful and direct late-stage formation of the F-ring in the hexacyclic core of himandrine drew on the power of biogenetic considerations and fully utilized the inherent chemistry of a plausible biosynthetic intermediate. |
| first_indexed | 2024-09-23T08:34:09Z |
| format | Article |
| id | mit-1721.1/71907 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T08:34:09Z |
| publishDate | 2012 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | mit-1721.1/719072022-09-30T09:38:44Z Total Synthesis of (−)-Himandrine Movassaghi, Mohammad Tjandra, Meiliana Qi, Jun Massachusetts Institute of Technology. Department of Chemistry Movassaghi, Mohammad Movassaghi, Mohammad Qi, Jun Tjandra, Meiliana We describe the first total synthesis of (−)-himandrine, a member of the class II galbulimima alkaloids. Noteworthy features of this chemistry include a diastereoselective Diels−Alder reaction in the rapid synthesis of the tricycle ABC-ring system in an enantiomerically enriched form, the use of a formal [3+3] annulation strategy to secure the CDE-ring system with complete diastereoselection, and successful implementation of our biogenetically inspired oxidative spirocyclization of an advanced intermediate. The successful and direct late-stage formation of the F-ring in the hexacyclic core of himandrine drew on the power of biogenetic considerations and fully utilized the inherent chemistry of a plausible biosynthetic intermediate. National Institute of General Medical Sciences (U.S.) (GM074825) 2012-07-31T13:09:54Z 2012-07-31T13:09:54Z 2009-06 2009-05 Article http://purl.org/eprint/type/JournalArticle 0002-7863 http://hdl.handle.net/1721.1/71907 Movassaghi, Mohammad, Meiliana Tjandra, and Jun Qi. “Total Synthesis of (−)-Himandrine.” Journal of the American Chemical Society 131.28 (2009): 9648-9650. https://orcid.org/0000-0003-3080-1063 en_US http://dx.doi.org/10.1021/ja903790y Journal of the American Chemical Society 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 PMC |
| spellingShingle | Movassaghi, Mohammad Tjandra, Meiliana Qi, Jun Total Synthesis of (−)-Himandrine |
| title | Total Synthesis of (−)-Himandrine |
| title_full | Total Synthesis of (−)-Himandrine |
| title_fullStr | Total Synthesis of (−)-Himandrine |
| title_full_unstemmed | Total Synthesis of (−)-Himandrine |
| title_short | Total Synthesis of (−)-Himandrine |
| title_sort | total synthesis of himandrine |
| url | http://hdl.handle.net/1721.1/71907 https://orcid.org/0000-0003-3080-1063 |
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