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Efficient and Stereoselective Dimerization of Pyrroloindolizine Derivatives Inspired by a Hypothesis for the Biosynthesis of Complex Myrmicarin Alkaloids

Movassaghi, Mohammad and Ondrus, Alison E. and Chen, Bin (2007) Efficient and Stereoselective Dimerization of Pyrroloindolizine Derivatives Inspired by a Hypothesis for the Biosynthesis of Complex Myrmicarin Alkaloids. Journal of Organic Chemistry, 72 (26). pp. 10065-10074. ISSN 0022-3263. PMCID PMC2992888. doi:10.1021/jo701981q. https://resolver.caltech.edu/CaltechAUTHORS:20170901-092017493

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Abstract

Pyrroloindolizine derivatives participate in efficient and stereoselective homo- and heterodimerization reactions upon treatment with Brønsted or Lewis acids. The distinctive ability of pyrroloindolizines to act as azafulvenium ion precursors provides direct access to both heptacyclic and hexacyclic dimeric products. The inherent reactivity of these structures suggests a concise synthesis of complex myrmicarin alkaloids, via dimerization of pyrroloindolizines, and may have implications for the biosynthesis of these intriguing alkaloids.


Item Type:Article
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https://doi.org/10.1021/jo701981qDOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo701981qPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jo701981q/suppl_file/jo701981q-file002.pdfPublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2992888/PubMed CentralArticle
Additional Information:© 2007 American Chemical Society. Received September 9, 2007. M.M. is a Firmenich Assistant Professor of Chemistry and a Beckman Young Investigator. A.E.O. acknowledges a Novartis Graduate Fellowship. We thank Professor Robert G. Griffin and Dr. Tony Bielecki for use of a high-field instrument at the MIT-Harvard Center for Magnetic Resonance (EB-002026). We thank Dr. Li Li for obtaining mass spectrometric data at the Department of Chemistry’s Instrumentation Facility, Massachusetts Institute of Technology. We thank Dr. Timothy E. Barder in the Buchwald group and Mr. Omar K. Ahmad for their assistance with DFT calculations. We are grateful for financial support by NIH-NIGMS (GM074825).
Funders:
Funding AgencyGrant Number
Arnold and Mabel Beckman FoundationUNSPECIFIED
NovartisUNSPECIFIED
NIHEB-002026
NIHGM074825
MIT-Harvard Center for Magnetic ResonanceUNSPECIFIED
Issue or Number:26
PubMed Central ID:PMC2992888
DOI:10.1021/jo701981q
Record Number:CaltechAUTHORS:20170901-092017493
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170901-092017493
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:81063
Collection:CaltechAUTHORS
Deposited By: Donna Wrublewski
Deposited On:01 Sep 2017 16:38
Last Modified:15 Nov 2021 19:40

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