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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,*
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 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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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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