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

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

doi:10.1021/acs.joc.5b01326

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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

Original language	English (US)
Pages (from-to)	8262-8267
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	80
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.5b01326
State	Published - Aug 21 2015

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.5b01326

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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 SN1-type ring closure catalyzed by DDQ to construct the 1,2-dioxepane ring.",

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AB - 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.

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

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