Issue 9, 2011
From the journal:

Organic & Biomolecular Chemistry

Vinylogous anionic processes in the formation and interconversion of tetracyclic ring systems†

Paul D. Thornton,a   T. Stanley Camerona  and  D. Jean Burnell*a  

* Corresponding authors

a Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada
E-mail: jean.burnell@dal.ca
Fax: +1 902-494-1310
Tel: +1 902 494-1664

Abstract

Tandem oxy-Cope and transannular vinylogous aldol reactions and/or vinylogous retro-aldol, conjugate addition, and transannular vinylogous aldol reactions transformed some tricyclic vinyl enones into fused tetracycles under basic conditions. Mesylates derived from similar tetracyclic products underwent efficient skeletal reorganization via transannular ring-opening but then different modes of transannular ring-closure upon treatment with tert-butoxide.

Graphical abstract: Vinylogous anionic processes in the formation and interconversion of tetracyclic ring systems

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Article information

DOI
https://doi.org/10.1039/C0OB01152E
Article type
Paper
Submitted
10 Dec 2010
Accepted
21 Feb 2011
First published
23 Feb 2011

Org. Biomol. Chem., 2011,9, 3447-3456

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Vinylogous anionic processes in the formation and interconversion of tetracyclic ring systems

P. D. Thornton, T. S. Cameron and D. J. Burnell, Org. Biomol. Chem., 2011, 9, 3447 DOI: 10.1039/C0OB01152E

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