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Issue 0, 1966
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The chemistry of hop constituents. Part XXIX. A synthesis of (±)-isohumulone

Abstract

(±)-Isohumulone has been synthesised by the reaction between 2-hydroxy-2,6-dimethylhept-3-yn-5-enoyl chloride and ethyl 5-methyl-2-oxohexanoate followed by cyclisation to give 4-hydroxy-3-(2-methylbutyryl)-4-(4-methylpent-1-yn-3-enyl)cyclopentane-1,3-dione, reaction of which with 1-bromo-3-methylbut-2-ene under alkaline conditions followed by hydration of the acetylenic group afforded (±)-isohumulone in low overall yield.

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Article information


J. Chem. Soc. C, 1966, 1615-1617
Article type
Paper

The chemistry of hop constituents. Part XXIX. A synthesis of (±)-isohumulone

P. R. Ashurst and D. R. J. Laws, J. Chem. Soc. C, 1966, 1615
DOI: 10.1039/J39660001615

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