| dc.contributor.author | Ondrus, Alison E. | |
| dc.contributor.author | Movassaghi, Mohammad | |
| dc.date.accessioned | 2012-10-05T17:14:06Z | |
| dc.date.available | 2012-10-05T17:14:06Z | |
| dc.date.issued | 2009-06 | |
| dc.date.submitted | 2009-04 | |
| dc.identifier.issn | 1523-7060 | |
| dc.identifier.issn | 1523-7052 | |
| dc.identifier.uri | http://hdl.handle.net/1721.1/73654 | |
| dc.description.abstract | 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. | en_US |
| dc.description.sponsorship | National Institute of General Medical Sciences (U.S.) (grant no. GM074825) | en_US |
| dc.description.sponsorship | National Institutes of Health (U.S.) (grant no. GM074825) | en_US |
| dc.language.iso | en_US | |
| dc.publisher | American Chemical Society | en_US |
| dc.relation.isversionof | http://dx.doi.org/10.1021/ol9008552 | 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 | Reversible Dimerization of (+)-Myrmicarin 215B | en_US |
| dc.type | Article | en_US |
| dc.identifier.citation | Ondrus, Alison E., and Mohammad Movassaghi. “Reversible Dimerization of (+)-Myrmicarin 215B.” Organic Letters 11.14 (2009): 2960–2963. | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
| dc.contributor.approver | Movassaghi, Mohammad | |
| dc.contributor.mitauthor | Movassaghi, Mohammad | |
| dc.contributor.mitauthor | Ondrus, Alison E. | |
| dc.relation.journal | Organic Letters | 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 | Ondrus, Alison E.; Movassaghi, Mohammad | en |
| dc.identifier.orcid | https://orcid.org/0000-0003-3080-1063 | |
| mit.license | PUBLISHER_POLICY | en_US |
| mit.metadata.status | Complete | |
