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

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.

Key words

hydrogenation - stereoselectivity - steric hindrance - (+)-nootkatone - valencanes

References and Notes

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Supporting Information contains pertinent 2D NMR.