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Radiochemical synthesis part II The preparation of 14C-labeled juvenile hormone by W. Hafferl; R. Zurflüh; L. Dunham is a Medicine article available to read on EtoBox.

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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

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Author
W. Hafferl; R. Zurflüh; L. Dunham
Publisher
John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0022-2135)
Published
1971
Language
EN
Field
Medicine (Life Sciences)

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