Diastereoselective brook rearrangement-mediated [3 + 4] annulation: Application to a formal synthesis of (+)-laurallene

Organic Letters

Volumn 10, Issue 9, 2008, Pages 1803-1806

  Sasaki, Michiko ^a   Hashimoto, Azusa ^a   Tanaka, Koudai ^a   Kawahata, Masatoshi ^b   Yamaguchi, Kentaro ^b   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; CHEMISTRY; RED ALGA; STEREOISOMERISM; SYNTHESIS;

ALGAE, RED; ETHERS, CYCLIC; STEREOISOMERISM;

EID: 48849106101     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8003595     Document Type: Article

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33. In this case, the use of lithium enolate resulted in a sluggish reaction in the stage of the oxidation even with the addition of an extra amount of NaHMDS and the crown ether.
34. The relative stereochemistry of the resulting alcohol was determined to be that shown after conversion into 2.
35. The use of oxalyl chloride gave much lower yield.