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 α,α′-disubstituted oxocene structure 16 through a Brook rearrangement-mediated [3 + 4] annulation using acryloylsilane 10 and 6-oxa-2-cycloheptenone 9 and...

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Bibliographic Details
Published in:Organic letters 2008-05, Vol.10 (9), p.1803-1806
Main Authors: Sasaki, Michiko, Hashimoto, Azusa, Tanaka, Koudai, Kawahata, Masatoshi, Yamaguchi, Kentaro, Takeda, Kei
Format: Article
Language:English
Subjects:
Ethers, Cyclic - chemical synthesis
Ethers, Cyclic - chemistry
Rhodophyta - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8003595