Tetrahedron p. 7727 - 7738 (1991)
Update date:2022-08-02
Topics:
Bailey, William F.
Khanolkar, Atmaram D.
The naturally occuring 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-endo-trig mode to give 1,1-dimethyl-2-(4-methylphenyl)cyclohexane.
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Doi:10.1002/ejic.201601227
(2017)Doi:10.1016/j.bmcl.2012.04.045
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(1991)Doi:10.1080/10426507.2012.655814
(2012)Doi:10.1039/P19910002894
(1991)
