Published July 16, 2009
| Supplemental Material + Accepted Version
Journal Article
Open
Reversible Dimerization of (+)-Myrmicarin 215B
- Creators
- Ondrus, Alison E.
- Movassaghi, Mohammad
Chicago
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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.
Additional Information
2009 American Chemical Society. Received April 18, 2009. M.M. is an Alfred P. Sloan Research Fellow and a Beckman Young Investigator. A.E.O. acknowledges a Novartis Graduate Fellowship. We are grateful for financial support by NIH-NIGMS (GM074825). We thank Dr. H. Ümit Kaniskan in our group for helpful discussions. We thank Professor Robert G. Griffin and Dr. Tony Bielecki at the MIT-Harvard Center for Magnetic Resonance for use of a high-field instrument (EB002026).Attached Files
Accepted Version - nihms127849.pdf
Supplemental Material - ol9008552_si_001.pdf
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ol9008552_si_001.pdf
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Additional details
- PMCID
- PMC2752850
- Eprint ID
- 81073
- DOI
- 10.1021/ol9008552
- Resolver ID
- CaltechAUTHORS:20170901-115555752
- Alfred P. Sloan Foundation
- Arnold and Mabel Beckman Foundation
- Novartis
- NIH
- GM-074825
- NIH
- EB-002026
- MIT-Harvard Center for Magnetic Resonance
- Created
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2017-09-01Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field