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Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation: Application to a Formal Synthesis of (+)-Laurallene

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journal contribution
posted on 01.05.2008, 00:00 by Michiko Sasaki, Azusa Hashimoto, Koudai Tanaka, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
The formal synthesis of (+)-laurallene, a halogenated eight-membered ring ether, was accomplished. The synthesis involves construction of a trans α,α′-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.