Total synthesis and study of myrmicarin alkaloids
The myrmicarins are a family of air- and temperature-sensitive alkaloids that possess unique structural features. Our concise enantioselective synthesis of the tricyclic myrmicarins enabled evaluation of a potentially biomimetic assembly of the complex members via direct dimerization of simpler stru...
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| Format: | Article |
| Language: | en_US |
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Royal Society of Chemistry
2013
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| Online Access: | http://hdl.handle.net/1721.1/82460 https://orcid.org/0000-0003-3080-1063 |
| _version_ | 1826202546434211840 |
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| author | Ondrus, Alison E. Movassaghi, Mohammad |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Ondrus, Alison E. Movassaghi, Mohammad |
| author_sort | Ondrus, Alison E. |
| collection | MIT |
| description | The myrmicarins are a family of air- and temperature-sensitive alkaloids that possess unique structural features. Our concise enantioselective synthesis of the tricyclic myrmicarins enabled evaluation of a potentially biomimetic assembly of the complex members via direct dimerization of simpler structures. These studies revealed that myrmicarin 215B undergoes efficient and highly diastereoselective Brønsted acid-induced dimerization to generate a new heptacyclic structure, isomyrmicarin 430A. Mechanistic analysis demonstrated that heterodimerization between myrmicarin 215B and a conformationally restricted azafulvenium ion precursor afforded a functionalized isomyrmicarin 430A structure in a manner that was consistent with a highly efficient, non-concerted ionic process. Recent advancement in heterodimerization between tricyclic derivatives has enabled the preparation of strategically functionalized hexacyclic structures. The design and synthesis of structurally versatile dimeric compounds has greatly facilitated manipulation of these structures en route to more complex myrmicarin derivatives. |
| first_indexed | 2024-09-23T12:09:13Z |
| format | Article |
| id | mit-1721.1/82460 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T12:09:13Z |
| publishDate | 2013 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | mit-1721.1/824602022-09-28T00:32:09Z Total synthesis and study of myrmicarin alkaloids Ondrus, Alison E. Movassaghi, Mohammad Massachusetts Institute of Technology. Department of Chemistry Ondrus, Alison E. Movassaghi, Mohammad The myrmicarins are a family of air- and temperature-sensitive alkaloids that possess unique structural features. Our concise enantioselective synthesis of the tricyclic myrmicarins enabled evaluation of a potentially biomimetic assembly of the complex members via direct dimerization of simpler structures. These studies revealed that myrmicarin 215B undergoes efficient and highly diastereoselective Brønsted acid-induced dimerization to generate a new heptacyclic structure, isomyrmicarin 430A. Mechanistic analysis demonstrated that heterodimerization between myrmicarin 215B and a conformationally restricted azafulvenium ion precursor afforded a functionalized isomyrmicarin 430A structure in a manner that was consistent with a highly efficient, non-concerted ionic process. Recent advancement in heterodimerization between tricyclic derivatives has enabled the preparation of strategically functionalized hexacyclic structures. The design and synthesis of structurally versatile dimeric compounds has greatly facilitated manipulation of these structures en route to more complex myrmicarin derivatives. Novartis (Firm) (Graduate Fellowship) National Institute of General Medical Sciences (U.S.) (GM074825) 2013-11-18T19:47:19Z 2013-11-18T19:47:19Z 2009-05 2009-02 Article http://purl.org/eprint/type/JournalArticle 1359-7345 1364-548X http://hdl.handle.net/1721.1/82460 Ondrus, Alison E., and Mohammad Movassaghi. “Total synthesis and study of myrmicarin alkaloids.” Chemical Communications, no. 28 (2009): 4151. https://orcid.org/0000-0003-3080-1063 en_US http://dx.doi.org/10.1039/b903995n Chemical Communications Creative Commons Attribution-Noncommercial-Share Alike 3.0 http://creativecommons.org/licenses/by-nc-sa/3.0/ application/pdf Royal Society of Chemistry PMC |
| spellingShingle | Ondrus, Alison E. Movassaghi, Mohammad Total synthesis and study of myrmicarin alkaloids |
| title | Total synthesis and study of myrmicarin alkaloids |
| title_full | Total synthesis and study of myrmicarin alkaloids |
| title_fullStr | Total synthesis and study of myrmicarin alkaloids |
| title_full_unstemmed | Total synthesis and study of myrmicarin alkaloids |
| title_short | Total synthesis and study of myrmicarin alkaloids |
| title_sort | total synthesis and study of myrmicarin alkaloids |
| url | http://hdl.handle.net/1721.1/82460 https://orcid.org/0000-0003-3080-1063 |
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