title: Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene.
abstract: A straightforward strategy for the syntheses of curcumene and ar-himachalene is reported. Synthetic highlights include a catalytic and asymmetric vinylogous Mukaiyama reaction and a stereospecific hydrogenolysis of a tertiary benzylic center using Pd/C or Ni/Raney catalysts. Notably, using Ni/Raney, the stereoselectivity outcome (inversion vs retention) of the hydrogenolysis depends on the tertiary benzylic alcohol substitution.
authors.affiliation: Institut Charles Gerhardt, UMR 5253 CNRS-UM-ENSCM, Ecole Nationale Supérieur de Chimie de Montpellier 8 , Rue de L'Ecole Normale, F-34296 Cedex 5 Montpellier, France.
authors.forename: Kim
authors.initials: K
authors.lastname: Spielmann
authors.affiliation: Institut Charles Gerhardt, UMR 5253 CNRS-UM-ENSCM, Ecole Nationale Supérieur de Chimie de Montpellier 8 , Rue de L'Ecole Normale, F-34296 Cedex 5 Montpellier, France.
authors.forename: Renata Marcia
authors.initials: RM
authors.lastname: de Figueiredo
authors.affiliation: Institut Charles Gerhardt, UMR 5253 CNRS-UM-ENSCM, Ecole Nationale Supérieur de Chimie de Montpellier 8 , Rue de L'Ecole Normale, F-34296 Cedex 5 Montpellier, France.
authors.forename: Jean-Marc
authors.identifier: 0000-0002-4943-047X
authors.initials: JM
authors.lastname: Campagne