133283-79-1Relevant academic research and scientific papers
Radical cyclization strategies to terpenoids; syntheses of (±)-β-cuparenone, (±)-laurene and epilaurenes
Srikrishna,Sundarababu
, p. 481 - 496 (2007/10/19)
Radical cyclization of the bromide 8, obtained in 5 steps from the ketone 9, furnished exclusively 14 via 6-endo frig cyclization with out any observable amount of 5-exo trig product 1. 5-Exo dig radical cyclization of the bromo acetate 23, prepared from
Construction of a Sterically Congested Carbon Framework via 5-Hexenyllithium Cyclization. Synthesis of (+/-)-Cuparene.
Bailey, William F.,Khanolkar, Atmaram D.
, p. 7727 - 7738 (2007/10/02)
The naturally occuring sesquiterpene (+/-)-cuparene , 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.
