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Synfacts 2008(9): 0898-0898  
DOI: 10.1055/s-2008-1077988
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of (+)-Laurallene

Contributor(s): Philip Kocienski, Zofia Komsta
M. Sasaki, A. Hashimoto, K. Tanaka, M. Kawahata, K. Yamaguchi, K. Takeda*
Hiroshima University and Tokushima Bunri University, Kagawa, Japan
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Publikationsdatum:
22. August 2008 (online)

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Significance

(+)-Laurallene has been isolated from the Laurencia sp. red algae. This formal synthesis focuses on the construction of the eight-membered ring ether via diastereoselective Brook rearrangement mediated [3+4] annulation (A + B → E). For the total synthesis of (+)-laurallene using intermediate J see: M. T. Crimmins,
E. A. Tabet J. Am. Chem. Soc. 2000, 122, 5473.