Diastereoselective Brook rearrangement-mediated [3+4] annulation: application to a formal synthesis of (+)-laurallene.
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.
Sasaki
Michiko
M
Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, Hiroshima, Japan.
Hashimoto
Azusa
A
Tanaka
Koudai
K
Kawahata
Masatoshi
M
Yamaguchi
Kentaro
K
Takeda
Kei
K
D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
D004988:Ethers, Cyclic