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An S<sub>N</sub>1‑type Reaction To Form the 1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene

By Justin A. Hilf (1545928), Luke W. Witthoft (1545925) and K. A. Woerpel (1312464)


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

Topics: Biophysics, Biochemistry, Physiology, Biotechnology, Marine Biology, Computational Biology, Chemical Sciences not elsewhere classified, Featured transformations, PeroxycalameneneThe, dioxepane, bicyclic core, peroxycalamenene, peroxidation, synthesis, intramolecular Heck reaction, DDQ, closure, sesquiterpene endoperoxide, Dioxepane, SN, Synthesi
Year: 2015
DOI identifier: 10.1021/acs.joc.5b01326.s001
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Provided by: FigShare
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