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Radiochemical synthesis part II The preparation of 14C-labeled juvenile hormone

✍ Scribed by W. Hafferl; R. Zurflüh; L. Dunham

Publisher
John Wiley and Sons
Year
1971
Tongue
French
Weight
423 KB
Volume
7
Category
Article
ISSN
0022-2135

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✦ Synopsis

dl-2-14C-Juvenile hormone was prepared from 2-1dC-trimethyl phosphonoacetate, sodium hydride and cis-9,iO-oxido-6-ethy~-iOmethy/dodec-5(t)-en-2-one in dry tetrahydrofuran and pur$ed by gas chromatography. The reaction conditions were established by synthesizing the trans-isomer of juvenile hormone. The specific activity of labeled hormone was determined by mass spectroscopy.

Juvenile hormone, a sesquiterpenoid compound which controls the normal maturation of insects has been shown by the elegant investigations of Roller and co-workers (2, 3, to have structure (Ill). The synthesis of juvenile hormone has been reported by a number of laboratories (4-7). The objective of our work was the preparation of milligram amounts of high specific activity lT-labeled juvenile hormone for biological studies.

Reaction of the anion of a trialkyl phosphonoacetate with carbonyl compounds provides an efficient general method for the synthesis of unsaturated esters @). The epoxyketone ([I) (cis-9, I0-oxido-6-ethyl-lO-rnethyldodec-5(t)en-bone) was prepared by selective terminal hydroxylation (osmium tetroxide/pyridine) of all-trans 6-ethyl-I O-methyldodeca-5,9-dien-2-one (9) to the 9, I O-diol (purified via its 3,5-dinitrobenzoate ester). Selective tosylation of this diol followed by base catalyzed internal elimination (potassium carbonate/ methanol) of the tosylate gave the cis-9,lO-epoxyketone (II), an ideal intermediate for radiochemical synthesis of juvenile hormone by the phosphonoacetate approach. The isotope could be incorporated in the last step of the synthesis by alkylation of ketone (IT) with the anion of 2-l4C-trjmethy1

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