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 inJournal of organic chemistry Vol. 82; no. 9; pp. 4737 - 4743
Main Authors Spielmann, Kim, de Figueiredo, Renata Marcia, Campagne, Jean-Marc
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.05.2017
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
KETONES
CROSS-COUPLING REACTIONS
ASYMMETRIC-SYNTHESIS
BENZYLIC ETHERS
ENANTIOSELECTIVE SYNTHESIS
VINYLOGOUS MUKAIYAMA REACTIONS
COMPONENT
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00419