title: Novel route to functionalized cyclooctanoids via [5+3] cycloaddition.
abstract: The self-dimerization of 3-oxidopyrylium leading to stereocontrolled formation of highly functionalized cyclooctanoids is described. Different functionalities were introduced on the dimer (3) and the stereochemical outcome was determined by single-crystal X-ray analysis. It is noteworthy that the hydrogenation of 3 in ethanol solvent gave the transannulated product 5, whereas the expected dihydro product 4 was obtained when the reaction was run in nonnucleophilic solvents. The mechanistic pathway is discussed.
authors.affiliation: Department of Chemistry, National Single-Crystal X-ray Diffraction Facility, Indian Institute of Technology Bombay, Mumbai 400076, India.
authors.forename: Urlam Murali
authors.initials: UM
authors.lastname: Krishna
authors.forename: Kodand D
authors.initials: KD
authors.lastname: Deodhar
authors.forename: Girish K
authors.initials: GK
authors.lastname: Trivedi
authors.forename: Shaikh M
authors.initials: SM
authors.lastname: Mobin