Diastereoselective Brook rearrangement-mediated [3+4] annulation: application to a formal synthesis of (+)-laurallene |
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Authors: | Sasaki Michiko Hashimoto Azusa Tanaka Koudai Kawahata Masatoshi Yamaguchi Kentaro Takeda Kei |
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Institution: | Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, Hiroshima, Japan. |
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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. |
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