Journal of the Chemical Society. Perkin transactions I p. 83 - 94 (1992)
Update date:2022-07-30
Topics:
Carling, Robert W.
Clark, J. Stephen
Holmes, Andrew B.
A general method for the construction of medium ring ethers is described in which a 2-substituted cycloalkanone was subjected to a Baeyer-Villiger ring expansion to the lactone, Tebbe methylenation of which afforded the enol ether which was subjected to a hydroboration-oxidation sequence to afford the 2,n-disubstituted oxacycle (n = ring size).Application of this procedure has led to efficient syntheses of the fully saturated skeletons corresponding to the naturally occurring Laurencia metabolites containing 2,n-dialkyl substituted seven- (isolaurepan), eight- (lauthisan and laurenan) and nine-membered (obtusan) ethers.
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