Total Synthesis of Liangshanone
Hongxiu Huang, Fen Mi, Chunxin Li, Huan He, Feng‐Peng Wang, Xiaoyu Liu, Yong Qin
Abstract
The first total synthesis of liangshanone, a hexacyclic ent-kaurane diterpenoid alkaloid, has been completed. Its intricate cagelike framework was assembled through several key transformations, including an oxidative dearomatization/Diels-Alder (OD/DA) cycloaddition sequence, a tandem alkene cleavage/Mannich cyclization, a Robinson-type annulation, and an intramolecular aldol reaction. Notably, an organocatalytic enantioselective α-hydroxymethylation process allowed the preparation of an enantiomerically enriched tricyclic intermediate that should enable asymmetric access to the target natural product.
Topics & Concepts
ChemistryAnnulationEnantioselective synthesisTotal synthesisCycloadditionStereochemistryIntramolecular forceAlkeneAldol reactionNatural productCombinatorial chemistryOrganic chemistryCatalysisPlant-based Medicinal ResearchBioactive Natural Diterpenoids ResearchAlkaloids: synthesis and pharmacology