- Synthesis of Substituted Cyclooctanols by a Samarium(II) Iodide Promoted 8-Endo Radical Cyclization Process
-
Samarium(II) iodide (SmI2) has been employed to promote an efficient 8-endo radical cyclization reaction of a variety of substituted olefinic ketones.Various substituted monocyclic, fused bicyclic, and bridged bicyclic cyclooctanols have been synthesized in fair to excellent yield via this protocol.In addition to delineating the synthetic potential of this reaction, experiments have been conducted to determine the source of reduced, noncyclized byproducts present in this and related SmI2-mediated reactions performed under protic conditions.
- Molander, Gary A.,McKie, Jeffrey A.
-
p. 3186 - 3192
(2007/10/02)
-
- Construction of a Sterically Congested Carbon Framework via 5-Hexenyllithium Cyclization. Synthesis of (+/-)-Cuparene.
-
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.
- Bailey, William F.,Khanolkar, Atmaram D.
-
p. 7727 - 7738
(2007/10/02)
-