Synthesis of 6, 14??ethenoisomorphinans and 6, 14??ethenomorphinans based on Diels??Alder adducts of 6??demethoxythebaine and 6??demethoxy?螃漫?dihydrothebaine; …

PR Crabbendam, TS Lie, JTM Linders…

Index: Crabbendam; Lie; Linders; Maat Recueil des Travaux Chimiques des Pays Bas, 1984 , vol. 103, # 10 p. 296 - 300

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Citation Number: 12

Abstract

Abstract Two different types of Diels-Alder additions to morphinan-6, 8-dienes have been found. 6-Demethoxythebaine (2) yielded ethyl 4, 5α-epoxy-3-methoxy-N-methyl-6, 14- ethenoisomorphinan–7α-carboxylate (3) with ethyl acrylate, in analogy to the reaction with thebaine. The ester 3 was converted into the alcohol 4, of which the 3-methoxy ether was hydrolyzed to yield 5. Similarly, 2 gave the 7α-acetyl-6, 14-ethenoisomorphinan 7 with ...