Synlett 2010(3): 445-448  
DOI: 10.1055/s-0029-1219206
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Hydrogenation Selectivity of the Bicyclo[4.4.0]decane Ring System of Valencanes

Anne M. Sauera, William E. Crowea, Gregg Hendersonb, Roger A. Laine*a,c
a Department of Chemistry, Louisiana State University and A&M College, Baton Rouge, LA 70803, USA
b Department of Entomology, The Louisiana State University Agricultural Center, Baton Rouge, LA 70803, USA
c Department of Biological Sciences, Louisiana State University and A&M College, Baton Rouge, LA 70803, USA
Fax: +1(225)2081148; e-Mail: rlaine@lsu.edu;
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Publikationsverlauf

Received 18 August 2009
Publikationsdatum:
15. Januar 2010 (online)

Abstract

To test the selectivity of sterically hindered systems, (+)-nootkatone and derivatives were subjected to a wide variety of hydrogenation methodologies. The steric impact of the C-4 methyl substituent seems to be responsible for the inability of the system to adopt the cis-fused structure.

3

Supporting Information contains pertinent 2D NMR.