%0 Journal Article
%T The Tandem Ring Opening/Ring Closing Metathesis Route to Oxaspirocycles: An Approach to Phelligridin G
%A Harold D. Cooper
%A Dennis L. Wright
%J Molecules
%D 2013
%I MDPI AG
%R 10.3390/molecules18022438
%X 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.
%K phelligridin G
%K Diels-Alder
%K spiroannulations
%K metathesis
%K 2-phenylfurans
%K natural products
%U http://www.mdpi.com/1420-3049/18/2/2438