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  • Title: A Concise Total Synthesis of (+)-Waihoensene Guided by Quaternary Center Analysis.
    Author: Peng C, Arya P, Zhou Z, Snyder SA.
    Journal: Angew Chem Int Ed Engl; 2020 Aug 03; 59(32):13521-13525. PubMed ID: 32330370.
    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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