Andransinine: an unusual case of spontaneous resolution in an indole alkaloid derivative
Yun-Yee Low1, Chew-Yan Gan, Toh-Seok Kam
1Department of Chemistry, Faculty of Science, University of Malaya , 50603 Kuala Lumpur, Malaysia.
Abstract:
Racemic andransinine (1), an indole alkaloid derivative obtained during isolation of alkaloids from Alstonia angustiloba and Kopsia pauciflora, was found to undergo spontaneous resolution when crystallized in EtOAc, forming racemic conglomerates (an equimolar mechanical mixture of enantiomerically pure individual crystals). X-ray analyses of the enantiomers (obtained from crystals from EtOAc solution and from chiral-phase HPLC) provided the absolute configuration of each enantiomer as (15R,16S,21R)-(+)-andransinine (1a or I+) and (15S,16R,21S)-(-)-andransinine (1b or I-).
More Related Videos
Related Concept Videos
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Drugs Affecting Neurotransmitter Release or Uptake
Adrenergic Agonists: Indirect-Acting Agents
One mechanism involves depleting stored catecholamines by displacing them from synaptic vesicles. These agents, known as "displacers," are transported into vesicles at the expense of noradrenaline. Examples include amphetamine and tyramine, which lack a catechol moiety, resulting in prolonged action, improved oral...
Cholinergic Antagonists: Chemistry and Structure-Activity Relationship
Phase I Reactions: Reductive Reactions
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview


