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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)
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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 (CC BY 3.0).

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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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