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

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journal contribution
posted on 21.08.2015, 00:00 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 SN1-type ring closure catalyzed by DDQ to construct the 1,2-dioxepane ring.