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

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,...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-05, Vol.82 (9), p.4737-4743
Main Authors: Spielmann, Kim, de Figueiredo, Renata Marcia, Campagne, Jean-Marc
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00419