2005•SynthesisRequires access
Total Synthesis of Japanese Hop Ether Using an Efficient Intramolecular Pauson-Khand Reaction
William J. Kerr, John Caldwell, Iain Cameron, S. Christie, Alastair M. Hay, Craig Johnstone, Anthony Murray
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Abstract
The naturally occurring monoterpene Japanese Hop Ether has been synthesised in 14 steps in an overall yield of 29%. The key step of the synthesis, an intramolecular Pauson-Khand reaction, has been shown to proceed in good to excellent yield under mild N-oxide promotion conditions and with complete retention of alkene stereochemistry (for both cis- and trans-alkenes) in the product cyclopentenone.