title: Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative.
abstract: The stereoselective Diels-Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 133-0033 Japan.
authors.forename: Toshiki
authors.initials: T
authors.lastname: Tabuchi
authors.forename: Daisuke
authors.initials: D
authors.lastname: Urabe
authors.forename: Masayuki
authors.initials: M
authors.lastname: Inoue
keywords: C2-symmetry; Diels–Alder reaction; Lewis acid; asymmetric synthesis; catalysis; natural product; quaternary carbon