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Syntheses de l'Acide (2R, 3S); (2S, 3R) Agarique ( 14 C‐4) et de l'Acide (2R, 3R); (2S, 3S) Agarique ( 3 H‐4,4,5,5)
Author(s) -
Lellouche J. P.,
Beaucourt J. P.,
Pichat L.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210206
Subject(s) - chemistry , diastereomer , dimethoxyethane , epoxide , hydrolysis , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , electrode , electrolyte , catalysis
(2R, 3S); (2S, 3R) [4‐ 14 C] Agaric acid and (2R, 3R); (2S, 3S) [4,4,5,5‐ 3 H] 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‐ 14 C] hexadecyl copper 10 . gave respectively the analog 4 of agaric acid trimethyl ester and methyl [4‐ 14 C]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 1 H‐NMR.