Abstract
C-10b Functionalized 5,6-dihydropyrrolo(2,1-a)isoquinolines have been prepared via Parham cyclization and α-amidoalkylation reactions, using functionalized organolithium reagents. Their utility as intermediates in the synthesis of erythrinanes via intra or intermolecular conjugate addition reactions has been studied. Thus, a protocol for preparing the erythrinane skeleton through a Parham cyclization−intermolecular α-amidoalkylation−intermolecular conjugate addition−ring-closing metathesis process has been described.
Highlights
The erythrinanes represent a significant class of alkaloids of broad pharmacological activity
Besides the curare–like and hypnotic action, they are known to display sedative, hypotensive, neuromuscular blocking, and CNS activity. This activity is attributed to antagonistic action of the nicotinic acetylcholine receptors in the brain.[1]. Because of their unique spiro amine structure and physiological activities, these alkaloids have been a target of synthesis for a long time.[2]
A notable characteristic of these processes is that products are armed with a readily functionalized substituent at C-10b, and that they posses the α,β-unsaturated lactam unit, which is suitable for conjugate addition reactions
Summary
The erythrinanes represent a significant class of alkaloids of broad pharmacological activity.
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