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Synthesis of 2-Dodecanoyl-3,5-dihydroxy-2-cyclohexen-1-one

✍ Scribed by James E. Oliver; Rolland M. Waters; William R. Lusby

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
402 KB
Volume
46
Category
Article
ISSN
0040-4020

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✦ Synopsis

Abatnd.

2-Dodccanoyl-3.5~dihydrox -2_cyclohexen-l-one, identified from the setal exudate of immature andromcda lace bug nymphs, Step hwJ tk takeyai, was synthcsixed. Key s s involved construction of the "E cyclohcxanaiione ring containing a phcn+iimcthylsilyl substitucnt as a masked ydmxyl group. protection of the 13_dicarbonyl system as an isoxaxole, odtive dcsilylation, and nductve disassembly of the isoxazolc.

For several yean we have been intuestcd in compounds scctetcd by lace bugs of the genus StepMrlsl' and of the. genus C~tythucha~'~. Fmm the lattcz we have identified 2-acyl-3,6dihydroxycyclohex-2cn-l-ones 3.4 , and have also recently reported the first synthesis of that novel class of compounds5. Continuing our investigations into the Sreph0rJfi.s genus, we examined the andnnneda lace bug, S. rukeyai, and identified three major components of irr exocrine sect&on as the chromanone 1, the 2,Gdihydroxyalkanaphenone 2, and the novel 2-&dccanoyl-3,5dihydroxycyclohcx-2co-l-one P. We hue report a synthesis of 3, undenaken to confirm the stmcmral assignment and to provide suffiient material to evaluate its proper&s.

Compound 3 is the enol of a 2-acylcyclohcxan-13dione. We wert unable to find likrature precedent for a 5-hydmxycyclohexan-1,3dione, with or without a 2-substituent. As a bhydroxykctonc, 3 would he expected to

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AJntract --Two of the title compounds. recently identified as components of exudates produced by lace bug nymphs of the genus Corythucha. have been synthesized. 2-Acyl-3-hydroxy-2-cyclohexen--l-ones were converted to 3-alkyd-6,7-dihydro-l,P-benzisoxazol-4(W)-ones which were hydroxylated at position

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## Abstract Relative rate coefficients for the reactions of OH with 3‐methyl‐2‐cyclohexen‐1‐one and 3,5,5‐trimethyl‐2‐cyclohexen‐1‐one have been determined at 298 K and atmospheric pressure by the relative rate technique. OH radicals were generated by the photolysis of methyl nitrite in synthetic a

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