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A short radiosynthesis of natural juvenile hormone III, methyl [12-3H]-(10R)-10,11-epoxyfarnesoate
- Source :
- Journal of Labelled Compounds and Radiopharmaceuticals. 25:627-633
- Publication Year :
- 1988
- Publisher :
- Wiley, 1988.
-
Abstract
- A new asymmetric synthesis of natural JH III from methyl farnesoate allows introduction of tritium from sodium borotritide into the 12-methyl group. Selective allylic oxidation followed by Sharpless epoxidation of the (E)-allylic alcohol gives an epoxy alcohol (>97% e.e.), which is oxidized to the aldehyde. Sodium borotritide (65 Ci/mmol) reduction of the aldehyde is followed by tosylation, iodide displacement, and cyanoborohydride displacement to give [3H]-(10R)-JH III, specific activity 14 Ci/mmol.
- Subjects :
- chemistry.chemical_classification
Sharpless epoxidation
Allylic rearrangement
organic chemicals
Organic Chemistry
Iodide
Radiosynthesis
Enantioselective synthesis
Alcohol
Biochemistry
Aldehyde
Medicinal chemistry
Analytical Chemistry
chemistry.chemical_compound
chemistry
Drug Discovery
Organic chemistry
Radiology, Nuclear Medicine and imaging
Specific activity
Spectroscopy
Subjects
Details
- ISSN :
- 03624803
- Volume :
- 25
- Database :
- OpenAIRE
- Journal :
- Journal of Labelled Compounds and Radiopharmaceuticals
- Accession number :
- edsair.doi...........bfadc8eabf85e228fde9997478fe770f