title: Diastereoselective Brook rearrangement-mediated [3+4] annulation: application to a formal synthesis of (+)-laurallene.
abstract: The formal synthesis of (+)-laurallene, a halogenated eight-membered ring ether, was accomplished. The synthesis involves construction of a trans alpha,alpha'-disubstituted oxocene structure 16 through a Brook rearrangement-mediated [3+4] annulation using acryloylsilane 10 and 6-oxa-2-cycloheptenone 9 and its conversion into 2, which has been transformed into (+)-laurallene by Crimmins and co-workers.
authors.affiliation: Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, Hiroshima, Japan.
authors.forename: Michiko
authors.initials: M
authors.lastname: Sasaki
authors.forename: Azusa
authors.initials: A
authors.lastname: Hashimoto
authors.forename: Koudai
authors.initials: K
authors.lastname: Tanaka
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Kawahata
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Kei
authors.initials: K
authors.lastname: Takeda
mesh_terms: D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004988:Ethers, Cyclic