Asymmetric Total Synthesis of (+)‐Mannolide C
Qiaoqiao Ao, Hai‐Jun Zhang, Jinbin Zheng, Xiaoming Chen, Hongbin Zhai
Abstract
Abstract (+)‐Mannolide C is a complex hexacyclic C 20 cephalotane‐type diterpenoid featuring a highly strained 7/6/6/5 tetracyclic core containing eight consecutive stereocenters and two bridging lactones. The first asymmetric total synthesis of (+)‐mannolide C has been accomplished by lipase‐mediated resolution, Ru‐complex‐catalyzed double ring‐closing metathesis (RCM) reactions, Ni II ‐catalyzed diastereoselective Michael addition, and Mn III ‐catalyzed allylic oxidation as the key transformations.
Topics & Concepts
ChemistryTotal synthesisStereochemistrySynthetic Organic Chemistry MethodsTraditional and Medicinal Uses of AnnonaceaePlant-derived Lignans Synthesis and Bioactivity