Thebaine adducts with maleimides. Synthesis and transformations

…, GA Tolstikov, VN Kalinin, G Schmidhammer

Index: Shults; Shakirov; Tolstikov; Kalinin; Schmidhammer Russian Journal of Organic Chemistry, 2005 , vol. 41, # 8 p. 1132 - 1144

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Citation Number: 7

Abstract

Abstract Diels-Alder reaction of thebaine with maleimides is structurally specific and yields [7, 8, 3′, 4′]-succinimido-endo-ethenotetrahydrothebaines containing N′-alkyl, cycloalkyl, aralkyl or aryl substituents. N′-[1 (S)-hydroxymethyl-2-methylpropyl]-succinimido- 6, 14-endo-ethenotetrahydrothebaine formed in reaction of S-valinol with (7α, 8α)-anhydrido- 6, 14-endo-ethenotetrahydrothebaine. The reduction of the adducts by LiAlH 4 afforded N ...