Total Synthesis of Japanese Hop Ether Using an Efficient Intramolecular Pauson-Khand Reaction

John J. Caldwell; Iain D. Cameron; Steven D. R. Christie; Alastair M. Hay; Craig Johnstone; William J. Kerr; Anthony Murray

doi:10.1055/s-2005-918459

PAPER

Total Synthesis of Japanese Hop Ether Using an Efficient Intramolecular Pauson-Khand Reaction

John J. Caldwell, Iain D. Cameron, Steven D. R. Christie, Alastair M. Hay, Craig Johnstone, William J. Kerr*, Anthony Murray
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland G1 1XL, UK
Fax: +44(141)5484246; e-Mail: w.kerr@strath.ac.uk;

Abstract

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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.

Key words

amine N-oxides - cyclopentenones - natural products - Pauson-Khand cyclizations - stereoselectivity

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References

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