Reversible Dimerization of (+)-Myrmicarin 215B
Brønsted acid promoted reversible dimerization of myrmicarin 215B leads to formation of a new heptacyclic product, isomyrmicarin 430B, that possesses a C1,C2-trans,C2,C3-trans-substituted cyclopentane ring. Mechanistic studies illustrate that isomyrmicarin 430B arises by isomerization of isomyrmicar...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society
2012
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| Online Access: | http://hdl.handle.net/1721.1/73654 https://orcid.org/0000-0003-3080-1063 |
| _version_ | 1826215473113464832 |
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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 | Brønsted acid promoted reversible dimerization of myrmicarin 215B leads to formation of a new heptacyclic product, isomyrmicarin 430B, that possesses a C1,C2-trans,C2,C3-trans-substituted cyclopentane ring. Mechanistic studies illustrate that isomyrmicarin 430B arises by isomerization of isomyrmicarin 430A via fragmentation to tricyclic azafulvenium ions. Factors influencing the structure of heptacyclic isomyrmicarin products and potential relevance of this reversible vinyl pyrroloindolizine dimerization to the biosynthesis of complex myrmicarins are discussed. |
| first_indexed | 2024-09-23T16:30:48Z |
| format | Article |
| id | mit-1721.1/73654 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:30:48Z |
| publishDate | 2012 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | mit-1721.1/736542022-09-29T20:00:41Z Reversible Dimerization of (+)-Myrmicarin 215B Ondrus, Alison E. Movassaghi, Mohammad Massachusetts Institute of Technology. Department of Chemistry Movassaghi, Mohammad Movassaghi, Mohammad Ondrus, Alison E. Brønsted acid promoted reversible dimerization of myrmicarin 215B leads to formation of a new heptacyclic product, isomyrmicarin 430B, that possesses a C1,C2-trans,C2,C3-trans-substituted cyclopentane ring. Mechanistic studies illustrate that isomyrmicarin 430B arises by isomerization of isomyrmicarin 430A via fragmentation to tricyclic azafulvenium ions. Factors influencing the structure of heptacyclic isomyrmicarin products and potential relevance of this reversible vinyl pyrroloindolizine dimerization to the biosynthesis of complex myrmicarins are discussed. National Institute of General Medical Sciences (U.S.) (grant no. GM074825) National Institutes of Health (U.S.) (grant no. GM074825) 2012-10-05T17:14:06Z 2012-10-05T17:14:06Z 2009-06 2009-04 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/73654 Ondrus, Alison E., and Mohammad Movassaghi. “Reversible Dimerization of (+)-Myrmicarin 215B.” Organic Letters 11.14 (2009): 2960–2963. https://orcid.org/0000-0003-3080-1063 en_US http://dx.doi.org/10.1021/ol9008552 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 PMC |
| spellingShingle | Ondrus, Alison E. Movassaghi, Mohammad Reversible Dimerization of (+)-Myrmicarin 215B |
| title | Reversible Dimerization of (+)-Myrmicarin 215B |
| title_full | Reversible Dimerization of (+)-Myrmicarin 215B |
| title_fullStr | Reversible Dimerization of (+)-Myrmicarin 215B |
| title_full_unstemmed | Reversible Dimerization of (+)-Myrmicarin 215B |
| title_short | Reversible Dimerization of (+)-Myrmicarin 215B |
| title_sort | reversible dimerization of myrmicarin 215b |
| url | http://hdl.handle.net/1721.1/73654 https://orcid.org/0000-0003-3080-1063 |
| work_keys_str_mv | AT ondrusalisone reversibledimerizationofmyrmicarin215b AT movassaghimohammad reversibledimerizationofmyrmicarin215b |