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

doi:10.3390/molecules18022438

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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

Harold D. Cooper^1,2 and Dennis L. Wright^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; in revised form: 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

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Cite This Article

MDPI and ACS Style

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.

AMA Style

Cooper HD, Wright DL. The Tandem Ring Opening/Ring Closing Metathesis Route to Oxaspirocycles: An Approach to Phelligridin G. Molecules. 2013; 18(2):2438-2448.

Chicago/Turabian Style

Cooper, Harold D.; Wright, Dennis L. 2013. "The Tandem Ring Opening/Ring Closing Metathesis Route to Oxaspirocycles: An Approach to Phelligridin G." Molecules 18, no. 2: 2438-2448.

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