An SN1‑type
Reaction To Form the
1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene

Hilf, Justin
A.; Witthoft, Luke W.; Woerpel, K. A.

doi:10.1021/acs.joc.5b01326.s001

jo5b01326_si_001.pdf (6.06 MB)

An S_N1‑type Reaction To Form the 1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene

journal contribution

posted on 2015-08-21, 00:00 authored by Justin A. Hilf, Luke W. Witthoft, K. A. Woerpel

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_N1-type ring closure catalyzed by DDQ to construct the 1,2-dioxepane ring.