Issue 6, 2013

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Feb 2013
Accepted
19 Mar 2013
First published
20 Mar 2013

Chem. Sci., 2013,4, 2364-2368

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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