Erythrina alkaloids are a rich source of complex polycyclic, bioactive natural products and more than 100 representatives have been identified to date. One of these alkaloids (+)-Dihydro-β-Erythroidine has been used in preclinical and clinical investigations as a selective antagonist of β2-containing heteromeric nicotine acetylcholine receptors. This alkaloid shows antidepressant-like activities in various animal models and is also effective as a muscle relaxant. The rich pharmacology and complex structural framework have made Erythrina Alkaloids attractive starting points for drug discovery and also popular targets for total synthesis, but (+)-Dihydro-β-Erythroidine have remained an elusive target until now. Herein we report the first enantioselective total synthesis of this alkaloid in 13 steps, relying on an asymmetric allylic alkylation to install the key α-tertiary amine stereo center in the first step and a decarboxylative cyanoacetate coupling to introduce the β,γ-lactone.<br/>

Enantioselective total synthesis of (+)-dihydro-β-erythroidine

2019 Fall National Meeting

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