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Syntheses de l'Acide (2R, 3S); (2S, 3R) Agarique (14C-4) et de l'Acide (2R, 3R); (2S, 3S) Agarique (3H-4,4,5,5)
- Source :
- Journal of Labelled Compounds and Radiopharmaceuticals. 21:125-132
- Publication Year :
- 1984
- Publisher :
- Wiley, 1984.
-
Abstract
- (2R, 3S); (2S, 3R) [4-14C] Agaric acid and (2R, 3R); (2S, 3S) [4,4,5,5-3H] agaric acid were synthesized from respectively threo methyl 1,2-epoxypropane-1,2,3-tricarboxylate 3 and erythro epoxide 2. Epoxy ring opening of 2 and 3 with [1-14C] hexadecyl copper 10. gave respectively the analog 4 of agaric acid trimethyl ester and methyl [4-14C]agaricate 5, which was hydrolyzed to 1a by lithium hydroxide in 1,2-dimethoxyethane (DME). Epoxy ring trans opening of 2 with diethyl 1-hexadecynylalane 9 gave the alcynyl derivative 7 which was saturated with tritium in presence of Pd/C to lead to 6. After hydrolysis (LiCH + DME), 1b was obtained. The structures of the diastereoisomers (2R, 3R); (2S, 3S) 1b and (2R, 3S); (2S, 3R) 1a rest on 1H-NMR.
- Subjects :
- Stereochemistry
Organic Chemistry
Agaric acid
Diastereomer
Epoxide
Ring (chemistry)
Biochemistry
Medicinal chemistry
Lithium hydroxide
Analytical Chemistry
chemistry.chemical_compound
Hydrolysis
chemistry
Drug Discovery
Radiology, Nuclear Medicine and imaging
Tritium
Spectroscopy
Derivative (chemistry)
Subjects
Details
- ISSN :
- 03624803
- Volume :
- 21
- Database :
- OpenAIRE
- Journal :
- Journal of Labelled Compounds and Radiopharmaceuticals
- Accession number :
- edsair.doi...........3ff25df68db2a31051a10f80bc6c0fc4
- Full Text :
- https://doi.org/10.1002/jlcr.2580210206