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Cycloaddition of Cyclohexa-2,4-dienones, Ring-Closing Metathesis, and Photochemical Reactions:  A Common Stereoselective Approach to Duprezianane, Polyquinane and Sterpurane Frameworks

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journal contribution
posted on 16.03.2007, 00:00 by Vishwakarma Singh, G. D. Praveena, Kapil Karki, Shaikh M. Mobin
A novel approach to three different types of carbocyclic frameworks belonging to dupreziananes, sterpuranes, and polyquinanes from simple aromatic precursors has been presented. Cycloaddition of appropriately appended cyclohexa-2,4-dienones with acyclic dienes gave bridged bicyclic octanes suitably disposed with olefinic chains, which upon ring-closing metathesis led to functionalized tricyclo[5.2.2.01,5]undecanes related to dupreziananes. Photochemical sigmatropic 1,2- and 1,3-acyl shifts in tricyclo[5.2.2.01,5] undecanes upon triplet and singlet excitation provided stereoselective routes to sterpurane and polyquinane frameworks.

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