Asymmetric Total Synthesis of Natural Lindenane Sesquiterpenoid Oligomers via a Triene as a Potential Biosynthetic Intermediate

Abstract

A previously proposed triene of the lindenane skeleton was synthesized, characterized, and identified as the common intermediate for the non‐enzymatic synthesis of natural lindenane oligomers through linear, [4+2]‐type and [6+6]‐type homo‐ and hetero‐ dimerization under simulated physiological conditions. As a result, the following six natural products were successfully synthesized through thermal head‐to‐head, head‐to‐tail, and head‐to‐back binding modes: shizukaols A and J, cycloshizukaol A, chlorahupetone F, chlotrichene B, and trishizukaol A.