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

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

Research output: Contribution to journalArticle

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<inf>N</inf>1-type ring closure catalyzed by DDQ to construct the 1,2-dioxepane ring.

Original languageEnglish (US)
Pages (from-to)8262-8267
Number of pages6
JournalJournal of Organic Chemistry
Volume80
Issue number16
DOIs
StatePublished - Aug 21 2015

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Sesquiterpenes
Peroxides
Cobalt
Biological Products
Functional groups
10,12-peroxycalamenene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

An S<inf>N</inf>1-type Reaction to Form the 1,2-Dioxepane Ring : Synthesis of 10,12-Peroxycalamenene. / Hilf, Justin A.; Witthoft, Luke W.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 80, No. 16, 21.08.2015, p. 8262-8267.

Research output: Contribution to journalArticle

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