Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation: Application to a Formal Synthesis of (+)-Laurallene
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- 作者：Michiko Sasaki ; Azusa Hashimoto ; Koudai Tanaka ; Masatoshi Kawahata ; Kentaro Yamaguchi ; Kei Takeda
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：May 1, 2008
- 年：2008
- 卷：10
- 期：9
- 页码：1803 - 1806
- 全文大小：107K
- 年卷期：v.10,no.9(May 1, 2008)
- ISSN：1523-7052
文摘
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.