Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines
A full account of our concise and enantioselective total syntheses of all known (−)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequenc...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2015
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| Online Access: | http://hdl.handle.net/1721.1/95510 https://orcid.org/0000-0003-3080-1063 |
| _version_ | 1826214200663343104 |
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| author | Han, Sunkyu Morrison, Karen C. Hergenrother, Paul J. Movassaghi, Mohammad |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Han, Sunkyu Morrison, Karen C. Hergenrother, Paul J. Movassaghi, Mohammad |
| author_sort | Han, Sunkyu |
| collection | MIT |
| description | A full account of our concise and enantioselective total syntheses of all known (−)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequence of transformations involving asymmetric oxidation and reorganization. Our enantioselective syntheses of these alkaloids enabled the revision of the absolute stereochemistry of (−)-trigonoliimines A, B, and C. We report that trigonoliimines A, B, C and structurally related compounds showed weak anticancer activities against HeLa and U-937 cells. |
| first_indexed | 2024-09-23T16:01:42Z |
| format | Article |
| id | mit-1721.1/95510 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:01:42Z |
| publishDate | 2015 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/955102022-10-02T05:45:38Z Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines Han, Sunkyu Morrison, Karen C. Hergenrother, Paul J. Movassaghi, Mohammad Massachusetts Institute of Technology. Department of Chemistry Movassaghi, Mohammad Han, Sunkyu A full account of our concise and enantioselective total syntheses of all known (−)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequence of transformations involving asymmetric oxidation and reorganization. Our enantioselective syntheses of these alkaloids enabled the revision of the absolute stereochemistry of (−)-trigonoliimines A, B, and C. We report that trigonoliimines A, B, C and structurally related compounds showed weak anticancer activities against HeLa and U-937 cells. National Institute of General Medical Sciences (U.S.) (GM074825) EMD Serono, Inc. (Graduate Fellowship) Kenneth Gordon Summer Fellowship 2015-02-25T15:39:40Z 2015-02-25T15:39:40Z 2013-10 2013-09 Article http://purl.org/eprint/type/JournalArticle 0022-3263 1520-6904 http://hdl.handle.net/1721.1/95510 Han, Sunkyu, Karen C. Morrison, Paul J. Hergenrother, and Mohammad Movassaghi. “Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines.” The Journal of Organic Chemistry 79, no. 2 (January 17, 2014): 473–486. https://orcid.org/0000-0003-3080-1063 en_US http://dx.doi.org/10.1021/jo4020358 Journal of Organic Chemistry 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 | Han, Sunkyu Morrison, Karen C. Hergenrother, Paul J. Movassaghi, Mohammad Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines |
| title | Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines |
| title_full | Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines |
| title_fullStr | Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines |
| title_full_unstemmed | Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines |
| title_short | Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines |
| title_sort | total synthesis stereochemical assignment and biological activity of all known trigonoliimines |
| url | http://hdl.handle.net/1721.1/95510 https://orcid.org/0000-0003-3080-1063 |
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