An S<sub>N</sub>1‑type
Reaction To Form the
1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene
- Publication date
- 2015
- Publisher
Abstract
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<sub>N</sub>1-type ring closure
catalyzed by DDQ to construct the 1,2-dioxepane ring