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)

J. P. Lellouche, J. P. Beaucourt, L. Pichat

Research output: Contribution to journalArticlepeer-review


(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.

Original languageFrench
Pages (from-to)125-132
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Issue number2
StatePublished - Feb 1984
Externally publishedYes

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