Synthesis of 1-(2,6,6-Trimethyl-4-hydroxy-1-cyclohexen-1-yl)-1,3-butanedione

doi:10.1271/BBB1961.46.2163

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Synthesis of 1-(2,6,6-Trimethyl-4-hydroxy-1-cyclohexen-1-yl)-1,3-butanedione

Published Aug 1, 1982 · Y. Tsujino, H. Kaneko

Agricultural and biological chemistry

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Abstract

Recently, Andersen et al. reported the isolation and structural elucidation of l-(2,6,6-trimethyl-4-hydroxy-lcyclohexenl-yl)-l,3-butanedione (1), an extracellular metabolite produced in laboratory cultures of the dinoflagellate Prorocentrum minimum.^ Although the diketone (1) was reported to show in vitro antibiotic activity against Staphylococcus aureus and to have the potential of being an excellent tracemetal chelator,1* the synthesis of (1) has not been reported yet.* Here we report the synthesis of l-(2,6,6-trimethyl-4hydroxy-1-cyclonexen-l-yl)-l,3-butanedione (1). As the starting material of the diketone (1), we chose 3-hydroxy/?-damascone (2) for which a convenient synthesis was recently reported.2) Epoxidation of the 3-hydroxy-/?-damascone (2) was carried out by usual basic peroxide oxidation using H2O2 and NaOH. The diastereomeric mixture of the epoxy ketone (3) was obtained in an excellent yeild (92%) without any other products. Conversion of the epoxy ketone (3) to the desired diketone (1) was carried out by the method of Suzuki et al., using Pd(0) as a catalyst.3) A mixture of the epoxy ketone (3), catalytic amounts of tetrakis(triphenylphosphine)palladium(O) and l ,2-bis(diphenylphosphino)ethane in toluene was placed in a sealed glass tube and heated under an argon atmosphere. Thereaction mixture was then purified with silica gel column chromatography (hexane-ether =6 : 4) followed by crystallization. The diketone (1) was obtained in an 80% yield. Although some differences were observed in the IR spectra, the *HNMR,13C-NMRand MSspectral data of the product completely coincided with those of the natural product. EXPERIMENTAL

Study Snapshot

This study successfully synthesized 1-(2,6,6-trimethyl-4-hydroxy-1-cyclohexen-1-yl)-1,3-butanedione (1), a potential antibiotic and tracemetal chelator, in an 80% yield from 3-hydroxy-?-damascone (2)

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis of 1-(2,6,6-Trimethyl-4-hydroxy-1-cyclohexen-1-yl)-1,3-butanedione

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