Total Synthesis of Leucosceptroids A and B

Abstract

Leucosceptroids A and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram‐scale total synthesis of leucosceptroid B and the first total synthesis of leucosceptroid A are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an (S)‐citronellal‐derived aldehyde, a SmI2‐mediated intramolecular ketyl–olefin radical cyclization, and final‐stage alcohol oxidation.

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

“…In 2013, Liu reported a synthesis of leucosceptroid B ( 308 ), 382 from 2014–2015 the group of Magauer reported the synthesis of eighteen leucosceptroids (including 307 and 308 ), 383,384 and in 2015, Ma reported a chiral pool approach to both 307 and 308 which will be discussed herein. 385 …”

Syntheses of Linear Biosynthetic C25-Precursors of Leucosceptroids

“…Intrigued by such diversity and polycyclic scaffolds, leucosceptroids have attracted much attention for their syntheses . The groups of Liu, Ma, and Magauer have already completed the total syntheses of several members of this natural product family.…”