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Molecules 2013, 18(2), 2438-2448; doi:10.3390/molecules18022438
Article

The Tandem Ring Opening/Ring Closing Metathesis Route to Oxaspirocycles: An Approach to Phelligridin G

1,2
 and
1,2,*
1 Department of Pharmaceutical Sciences, University of Connecticut, Storrs, CT 06269, USA 2 Department of Chemistry, University of Connecticut, Storrs, CT 06269, USA
* Author to whom correspondence should be addressed.
Received: 4 December 2012 / Revised: 31 January 2013 / Accepted: 7 February 2013 / Published: 21 February 2013
(This article belongs to the Special Issue Spiro Compounds)
Download PDF [310 KB, 18 June 2014; original version 18 June 2014]

Abstract

Phelligridin G is an unusual natural product that contains an embedded spiro-fused furanone core. We have investigated two furan-based synthetic approaches towards the spirocyclic core structure of this natural product from readily available 2-phenylfurans. Although initial studies involving an oxidative cyclization were unsuccessful, we were ultimately able to access this key system through a sequential intermolecular furan Diels-Alder reaction followed by a metathesis-based reorganization. A related approach led to an expanded C ring to form spiro-fused pyran spirocycles.
Keywords: phelligridin G; Diels-Alder; spiroannulations; metathesis; 2-phenylfurans; natural products phelligridin G; Diels-Alder; spiroannulations; metathesis; 2-phenylfurans; natural products
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Cooper, H.D.; Wright, D.L. The Tandem Ring Opening/Ring Closing Metathesis Route to Oxaspirocycles: An Approach to Phelligridin G. Molecules 2013, 18, 2438-2448.

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