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Published December 21, 2007 | Accepted Version + Supplemental Material
Journal Article Open

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

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.

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).

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Accepted Version - nihms63561.pdf

Supplemental Material - jo701981q-file002.pdf

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Created:
August 19, 2023
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October 17, 2023