Concise and Scalable Total Syntheses of Lamellarin Z and other Natural Lamellarins

Abstract

Abstract An efficient construction of the central 1,2,4‐trisubstituted pyrrole core via one‐pot [3+2] cycloaddition/elimination/aromatization sequence‐based domino process and subsequent Pd‐mediated cross dehydrogenative coupling between the C−H bonds of pyrrole and the peripheral aryl rings enables rapid access to the pentacyclic coumarin‐pyrrole‐isoquinoline scaffolds which were smoothly elaborated to the targeted lamellarins alkaloids. The total synthesis of lamellarins Z and S with the highest overall yield reported till date, besides the synthesis of several other natural lamellarins have been realized in 5–6 steps with overall yields ranging from 20–27 %.

Topics & Concepts