| dc.contributor.author | Han, Sunkyu | |
| dc.contributor.author | Morrison, Karen C. | |
| dc.contributor.author | Hergenrother, Paul J. | |
| dc.contributor.author | Movassaghi, Mohammad | |
| dc.date.accessioned | 2015-02-25T15:39:40Z | |
| dc.date.available | 2015-02-25T15:39:40Z | |
| dc.date.issued | 2013-10 | |
| dc.date.submitted | 2013-09 | |
| dc.identifier.issn | 0022-3263 | |
| dc.identifier.issn | 1520-6904 | |
| dc.identifier.uri | http://hdl.handle.net/1721.1/95510 | |
| dc.description.abstract | 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. | en_US |
| dc.description.sponsorship | National Institute of General Medical Sciences (U.S.) (GM074825) | en_US |
| dc.description.sponsorship | EMD Serono, Inc. (Graduate Fellowship) | en_US |
| dc.description.sponsorship | Kenneth Gordon Summer Fellowship | en_US |
| dc.language.iso | en_US | |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | http://dx.doi.org/10.1021/jo4020358 | en_US |
| dc.rights | 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. | en_US |
| dc.source | PMC | en_US |
| dc.title | Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines | en_US |
| dc.type | Article | en_US |
| dc.identifier.citation | 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. | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
| dc.contributor.mitauthor | Movassaghi, Mohammad | en_US |
| dc.contributor.mitauthor | Han, Sunkyu | en_US |
| dc.relation.journal | Journal of Organic Chemistry | en_US |
| dc.eprint.version | Author's final manuscript | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dspace.orderedauthors | Han, Sunkyu; Morrison, Karen C.; Hergenrother, Paul J.; Movassaghi, Mohammad | en_US |
| dc.identifier.orcid | https://orcid.org/0000-0003-3080-1063 | |
| mit.license | PUBLISHER_POLICY | en_US |
| mit.metadata.status | Complete | |
