Seychellanes

In an elegant new synthetic route to ( )-seychellene (610) cf. Vol. 4, p. 139 Vol. 5, p. 89), the bicyclo[2,2,2]octanone intermediate (608) is constructed by Diels-Alder reaction between a 2-silyloxydiene (607) and methyl vinyl ketone. Subsequent conversion of the product (608) into the seychellane framework involves intramolecular alkylation of the derived bromo-ketone (609) (Scheme 66). 

Seychellane type Patchouliane type Patchoulane type... 

Cycloseychellene (187) is a new seychellane sesquiterpene which co-occurs with seychellene (183) (269). An acid catalyzed equilibration between these two compounds has been achieved by reaction of either isomer wich cupric acetate in acetic acid, the equilibrium favoring seychellene (269). 

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