title: Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis, and photochemical reactions: a common stereoselective approach to duprezianane, polyquinane and sterpurane frameworks.
abstract: 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[5.2.2.0(1,5)]undecanes related to dupreziananes. Photochemical sigmatropic 1,2- and 1,3-acyl shifts in tricyclo[5.2.2.0(1,5)] undecanes upon triplet and singlet excitation provided stereoselective routes to sterpurane and polyquinane frameworks.
authors.affiliation: Department of Chemistry and National Single X-ray Diffraction Facility, Indian Institute of Technology, Bombay, Mumbai 400 076, India. vks@chem.iitb.ac.in
authors.forename: Vishwakarma
authors.initials: V
authors.lastname: Singh
authors.forename: G D
authors.initials: GD
authors.lastname: Praveena
authors.forename: Kapil
authors.initials: K
authors.lastname: Karki
authors.forename: Shaikh M
authors.initials: SM
authors.lastname: Mobin