Issue 1, 2011
From the journal:

Chemical Communications

An efficient oxidative dearomatization–radical cyclization approach to symmetrically substituted bicyclic guttiferone natural products†‡

Nicholas A. McGrath,a   Joshua R. Binner,a   Georgios Markopoulos,a   Matthew Brichaceka  and  Jon T. Njardarson*a  

* Corresponding authors

a Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY, USA
E-mail: jn96@cornell.edu
Fax: +1 607 255 4137
Tel: +1 607 254 5035

Abstract

Detailed in this communication is an efficient synthetic approach towards the guttiferone family of natural products. Oxidatively unraveling a para-quinone monoketal followed by consecutive 5-exo radical cyclizations provides the bicyclic core. An additional strength of this approach is a late stage asymmetric desymmetrization of an advanced symmetric intermediate.

Graphical abstract: An efficient oxidative dearomatization–radical cyclization approach to symmetrically substituted bicyclic guttiferone natural products

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Article information

DOI
https://doi.org/10.1039/C0CC01419B
Article type
Communication
Submitted
14 May 2010
Accepted
18 Jun 2010
First published
07 Jul 2010

Chem. Commun., 2011,47, 209-211

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An efficient oxidative dearomatization–radical cyclization approach to symmetrically substituted bicyclic guttiferone natural products

N. A. McGrath, J. R. Binner, G. Markopoulos, M. Brichacek and J. T. Njardarson, Chem. Commun., 2011, 47, 209 DOI: 10.1039/C0CC01419B

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