142285-26-5Relevant articles and documents
Synthesis of Medium Ring Ethers. Part 2. Synthesis of the Fully Saturated Carbon Skeleton of Laurencia Non-terpenoid Ether Metabolites Containing Seven-, Eight- and Nine-membered Rings
Carling, Robert W.,Clark, J. Stephen,Holmes, Andrew B.
, p. 83 - 94 (2007/10/02)
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.