title: Synthesis of the trans-hydrindane core of dictyoxetane.
abstract: A concise, stereoselective synthesis of the trans-hydrindane core of the marine natural product dictyoxetane is reported, starting from a Robinson annelation derived bicyclic enone. A phosphorane-mediated, pinacol-like rearrangement of a cis-diol, via a formal 1,2-hydride shift, is used to establish the requisite trans ring junction. (31)P NMR supports the formation of the intermediate phosphorane, generated in situ from the reaction of a diol with Ph(3)PCl(2).
authors.affiliation: School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
authors.forename: Benedicte
authors.initials: B
authors.lastname: Defaut
authors.forename: Thomas B
authors.initials: TB
authors.lastname: Parsons
authors.forename: Neil
authors.initials: N
authors.lastname: Spencer
authors.forename: Louise
authors.initials: L
authors.lastname: Male
authors.forename: Benson M
authors.initials: BM
authors.lastname: Kariuki
authors.forename: Richard S
authors.initials: RS
authors.lastname: Grainger
mesh_terms: D004224:Diterpenes / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D007189:Indans; C574909:dictyoxetane; C531997:hydrindane