Abstract
An indolizidine alkaloid, (+)-ipalbidine, exhibiting a non-addictive analgesic activity, was synthesized in an optically active form, by employing an intramolecular McMurry coupling reaction as a key step.
Highlights
Indolizidine alkaloids, a large class of natural products, are popular synthetic targets because they exhibit attractive biological activity and provide further opportunities for developing new synthetic methods and strategies for the nitrogen-heterocyclic ring systems
Owing to its interesting biological activity, a number of total syntheses for racemic ipalbidine has been reported by several groups.[4]
Only one chiral synthesis for ipalbidine has appeared to date,[5] where, the specific optical rotation of the synthesized compound [α]D +54.1 (c=1, EtOH) was found to be much different from that of the optically resolved compound [α]D +190.5 (c=1, MeOH).4b As an extension of our work on the synthesis of analgesic agents, we are interested in a total synthesis of (+)-ipalbidine in an optically pure form
Summary
Indolizidine alkaloids, a large class of natural products, are popular synthetic targets because they exhibit attractive biological activity and provide further opportunities for developing new synthetic methods and strategies for the nitrogen-heterocyclic ring systems. The direct formation of the alkene function from the diketone 12 by employing McMurry coupling as the key step gave the desired product, which led to the chiral synthesis of the target natural product, the yield was found to be unsatisfactory.
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