An S(N)1-type Reaction To Form the 1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene

作者:Hilf Justin A; Witthoft Luke W; Woerpel K A*
来源:Journal of Organic Chemistry, 2015, 80(16): 8262-8267.
DOI:10.1021/acs.joc.5b01326

摘要

The synthesis of the sesquiterpene endoperoxide natural product 10,12-peroxycalamenene has been achieved. Featured transformations include an intramolecular Heck reaction to build the fused bicyclic core and a cobalt-catalyzed peroxidation to install the peroxide functional group. The final step involved an S(N)1-type ring closure catalyzed by DDQ to construct the 1,2-dioxepane ring.

  • 出版日期2015-8-21