Total synthesis of cyclic diterpene tonantzitlolone based on a highly stereoselective substrate-controlled aldol reaction and ring-closing metathesis

Abstract

The total synthesis of the cyclic diterpene ent-tonantzitlolone (ent-1) is presented. Key steps for assembling the macrocyclic core structure of 1 are a highly selective aldol reaction and an E selective ring-closing metathesis reaction. A detailed investigation of these two steps and the final transformations towards the completion of the synthesis is disclosed.