Construction of the Tetracyclic Core of Harziandione via Gold(I) Catalysis
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Updated: May 17, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Jiachen Deng1, Ganlin Huang1, Jinghan Gui1,2
1State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China.
Abstract:
Harziandione is a diterpenoid natural product featuring a 6/5/7/4 tetracyclic core with four contiguous stereocenters, two of which are quaternary. Herein, we report the rapid assembly of its tetracyclic framework in just nine steps from commercially available cyclopentenone, strategically enabled by gold(I) catalysis. The strained bicyclo[5.2.0]nonene motif was assembled via a gold(I)-catalyzed formal [2 + 2] cycloaddition, while the congested bridged [3.2.1] ring system was constructed through a gold(I)-catalyzed Conia-ene reaction. Subsequently, the pivotal C11 enone was installed using a sequence featuring olefin dihydroxylation and Babler-Dauben oxidation as key transformations.
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