Abstract
The naturally occurring sesquiterpene (±)-cuparene [1,1,2-trimethyl-2-(4-methylphenyl)cyclopentane], which contains two contiguous quaternary centers, is produced in good yield by 5-exo-trig cyclization of the 5-hexenyllithium ( 2) generated from 6-iodo-3,3-dimethyl-2-(4-methylphenyl)-1-hexene ( 3) by low temperature lithium - iodine exchange. In contrast, radical mediated cyclization of 3 proceeds via the 6-endotrig mode to give 1,1-dimethyl-2-(4-methylphenyl)cyclohexane.
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