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Issue 6, 2013
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A radical-based approach for the construction of the tetracyclic structure of resiniferatoxin

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Abstract

A novel radical-based strategy for accessing the unique tetracyclic skeleton of resiniferatoxin is described. The synthetic route is characterized by a stereoselective synthesis of the C-ring which has a bridgehead O,Se–acetal, a three component radical coupling of the A- and C-rings and a branched allyl stannane, and a 7-endo radical cyclization to construct the fused B-ring from the coupling adduct. The present approach attests to the power of radical reactions to realize the congested C–C bond formations required for synthesizing highly functionalized compounds.

Graphical abstract: A radical-based approach for the construction of the tetracyclic structure of resiniferatoxin

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Publication details

The article was received on 05 Feb 2013, accepted on 19 Mar 2013 and first published on 20 Mar 2013


Article type: Edge Article
DOI: 10.1039/C3SC50329A
Chem. Sci., 2013,4, 2364-2368

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    A radical-based approach for the construction of the tetracyclic structure of resiniferatoxin

    K. Murai, S. Katoh, D. Urabe and M. Inoue, Chem. Sci., 2013, 4, 2364
    DOI: 10.1039/C3SC50329A

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