title: An SN1-type Reaction To Form the 1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene.
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.
authors.affiliation: Department of Chemistry, New York University, New York, New York 10003, United States.
authors.forename: Justin A
authors.initials: JA
authors.lastname: Hilf
authors.affiliation: Department of Chemistry, New York University, New York, New York 10003, United States.
authors.forename: Luke W
authors.initials: LW
authors.lastname: Witthoft
authors.affiliation: Department of Chemistry, New York University, New York, New York 10003, United States.
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C096076:10,12-peroxycalamenene; D010082:Oxepins; D012717:Sesquiterpenes