Synthesis of 3-Oxaterpenoids and Its Application in the Total Synthesis of (±)-Moluccanic Acid Methyl Ester

摘要

3-Oxaterpenoids represent an important class of plant-based natural products and drugs, are oxidative metabolites of terpenoids, and exhibit interesting biological activities and pharmaceutical potentials (Figure l). For example, salvi- norin A (A) is a selective K-opioid-receptor agonist, compound B is a mild toxin to brine shrimp, and compound C shows significant cytotoxic activity. Captivated by the intricate polycyclic structure and diverse bioactivities of 3-oxaterpenoids, and inspired by Nature's uncanny workmanship in constructing them, we were very interested in the development of efficient methods to complement the biosynthesis. Herein, we report the preparation of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester, through a cascade of Prins reaction and polyene cyclization (Scheme 1).