In -sinularene synthesi

Several sesquiterpenes have been synthesized using this methodology. Bicyclo[3.2.1]octadiene 92, obtained in excellent yield from 91, has been used in the synthesis of prezizaene (93). Other targets included sinularene (94) and quadrone (95). ... 

A synthesis of the unique marine sesquiterpenoid sinularene (212) has been achieved by a route which closely parallels the methodology used by Money et to synthesize copacamphor and ylangocamphor (Scheme 25). Full details of the very interesting synthesis of cyclosativene (215) have been published. As shown in Scheme 26, the critical synthetic step involves the solvolysis of the bicyclic tosylate (213) which proceeds by intramolecular capture of the cyclo-propylcarbinyl cation by the pendant acetylene group to afford (214). 

Kingston, J.F., Ng, A.S., Gallacher, G and Fallis, A.G. (1983) Studies in marine organic chemistry marine natural products from invertebrates foimd in Newfoundland waters and approaches to the total synthesis of sinularene. Mar. Chem., 12,147-157. 

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