Total Synthesis of Liangshanone |
| |
Authors: | Hong-Xiu Huang Fen Mi Chunxin Li Huan He Prof. Dr. Feng-Peng Wang Prof. Dr. Xiao-Yu Liu Prof. Dr. Yong Qin |
| |
Affiliation: | Key Laboratory of Drug Targeting and Drug Delivery Systems of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drugs and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041 China |
| |
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. |
| |
Keywords: | alkaloids cycloaddition domino reactions ent-kaurane diterpenoids total synthesis |
|
|