Scandium-Catalyzed Voigt Condensation Enables One-Step Synthesis of Lathyranone-Type Nitrogen-Containing Euphorbia
Wei Cheng1, Pei-Yin Song1, Lian Sun1
1Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, People's Republic of China.
Abstract:
A series of 6/11/3 lathyranone-type nitrogen-containing diterpenoids (3a-3v) were efficiently synthesized in one step from naturally abundant 5/11/3 lathyranes via a Sc(OTf)3-promoted Voigt condensation. The reaction features mild conditions, a broad substrate scope, and good substrate-induced stereoselectivity. This work establishes an efficient route for the convenient synthesis of diverse lathyranone derivatives and has led to the discovery of a promising antitumor nitrogen-containing diterpenoid 4b.
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