Pavinan and isopavinan alkaloids. Synthesis of racemic and natural thalidine, bisnorargemonine, and congeners from N-norreticuline

…, WC Ripka, J Reden, A Brossi

Index: Rice, Kenner C.; Ripka, W. C.; Reden, J.; Brossi, A. Journal of Organic Chemistry, 1980 , vol. 45, # 4 p. 601 - 607

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Citation Number: 23

Abstract

The isopavinan alkaloids thalidine and 0-methylthalisopavine and the pavinan alkaloids bisnorargemonine and argemonine were synthesized as the racemates and natural isomers from the appropriate form of N-norreticuline. The sequence utilizing (S)-(-)-N-norreticuline afforded the natural alkaloids and confirmed the absolute stereochemistry previously assigned to these compounds by several methods. The tetracyclic skeleton of both ...