Total synthesis of selected tyrosine‐derived alkaloids: A comparative analysis of tyrosine‐based chiral pool vs other synthetic approaches

Abstract

AbstractAlkaloids are secondary metabolites and they continue to be investigated owing to their mesmerizing architectural features having potent medicinal properties. Due to the presence of stereogenic center resulting into inherent chirality and configurational integrity, alkaloids have become the area under the countless discussion in synthetic studies. In biological systems, uniqueness of tyrosine rests on phenolic −OH which acts as both hydrogen bond donor, acceptor and its aromatic ring is capable of engaging in π–π stacking interactions. Moreover, tyrosine serves as an economical and adaptable chiral pool in asymmetric synthesis of alkaloids. Herein, we discussed total syntheses of selected alkaloids via tyrosine and non‐tyrosine‐based routes along with comparison of synthetic steps based on strategy, total number of steps, use of complex reagents, overall yield, ee etc. It is first critical review about tyrosine as a chiral pool over other strategies towards alkaloids.