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Updated: Dec 23, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
A Concise Total Synthesis of (+)-Waihoensene Guided by Quaternary Center Analysis
Cheng Peng1, Piyush Arya1, Zhiyao Zhou1
1Department of Chemistry, University of Chicago, 5735 S. Ellis Avenue, Chicago, IL, 60637, USA.
Abstract:
The four contiguous all-carbon quaternary centers of waihoensene, coupled with the absence of any traditional reactive functional groups other than a single alkene, render it a particularly challenging synthetic target among angular triquinane natural products. Here, we show that its polycyclic frame can be assembled concisely by using a strategically chosen quaternary center to guide the formation of the other three through judiciously selected C-C bond formation reactions. Those events, which included a unique Conia-ene cyclization and a challenging Pauson-Khand reaction, afforded a 17-step synthesis of the molecule in enantioenriched form.
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