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Dimerization of (+)-myrmicarin 215B. A potential biomimetic approach to complex myrmicarin alkaloids

Ondrus, Alison E. and Movassaghi, Mohammad (2006) Dimerization of (+)-myrmicarin 215B. A potential biomimetic approach to complex myrmicarin alkaloids. Tetrahedron, 62 (22). pp. 5287-5297. ISSN 0040-4020. PMCID PMC2904612. https://resolver.caltech.edu/CaltechAUTHORS:20170901-085936823

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Abstract

The acid promoted diastereoselective dimerization of myrmicarin 215B is described. The reactivity of these sensitive alkaloids, structural assignment, and a possible mechanism for the observed dimerization is discussed. These finding raise the intriguing possibility of the synthesis of the highly sensitive myrmicarin alkaloids based on a strategy involving the direct dimerization of functional tricyclic myrmicarin derivatives.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1016/j.tet.2006.01.108DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040402006002857PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2904612/PubMed CentralArticle
Additional Information:Ⓒ 2006 Elsevier Ltd. Received 19 December 2005; revised 27 December 2005; accepted 3 January 2006. M.M. is a Dale F. and Betty Ann Frey Damon Runyon Scholar supported by the Damon Runyon Cancer Research Foundation (DRS-39-04). M.M. is a Firmenich Assistant Professor of Chemistry. 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). The MIT-DCIF is supported in part by NSF (CHE-9808061 and DBI-9729592) and NIH (1S10RR13886-01). We are grateful for the financial support by the American Chemical Society PRF (40631G1), MIT, Amgen Inc., and NIHNIGMS (GM074825).
Funders:
Funding AgencyGrant Number
Damon Runyon Cancer Research FoundationDRS-39-04
NovartisUNSPECIFIED
NIHEB-002026
NSFCHE-9808061
NSFDBI-9729592
NIH1S10RR13886-01
American Chemical Society Petroleum Research Fund40631G1
Massachusetts Institute of Technology (MIT)UNSPECIFIED
AmgenUNSPECIFIED
NIHGM074825
MIT-Harvard Center for Magnetic ResonanceUNSPECIFIED
Issue or Number:22
PubMed Central ID:PMC2904612
Record Number:CaltechAUTHORS:20170901-085936823
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170901-085936823
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:81060
Collection:CaltechAUTHORS
Deposited By: Donna Wrublewski
Deposited On:01 Sep 2017 16:48
Last Modified:03 Oct 2019 18:38

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