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
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 83-94
- https://doi.org/10.1039/p19920000083
Abstract
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.Keywords
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