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Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene. | LitMetric

Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene.

J Org Chem

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.

Published: May 2017

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.

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Source
http://dx.doi.org/10.1021/acs.joc.7b00419DOI Listing

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