Total synthesis of strictamine: a tutorial for novel and efficient synthesis

Abstract

When teaching synthetic design in the classroom, the novelty and efficiency of the overall synthetic route are the key values being imparted to the younger generation of synthetic chemists. The creative synthetic design is of great interest to graduate students who are entering into this exciting field for the first time. Strictamine, an akuammiline alkaloid, bears a congested cage-like structure and has interesting biological activities. Numerous attempts have been made toward the total synthesis of this compound since its discovery five decades ago. The synthesis was not completed until last year when synthetic chemists began to apply novel ring construction strategies. In 2016, two research groups reported the total syntheses of strictamine and four reported the formal syntheses. In this Highlight, the synthesis of strictamine is used as a tutorial case to illustrate novelty and efficiency in total synthesis.