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  • Title: Asymmetric Total Synthesis of (+)-Waihoensene.
    Author: Qu Y, Wang Z, Zhang Z, Zhang W, Huang J, Yang Z.
    Journal: J Am Chem Soc; 2020 Apr 08; 142(14):6511-6515. PubMed ID: 32203659.
    Abstract:
    The asymmetric total synthesis of (+)-waihoensene, which has a cis-fused [6,5,5,5] tetracyclic core bearing an angular triquinane, a cis-fused six-membered ring, and four contiguous quaternary carbon atoms, was achieved through a sequence of chemical reactions in a stereochemically well-defined manner. The total synthesis features the following: (1) Cu-catalyzed asymmetric conjugated 1,4-addition; (2) diastereoselective Conia-ene type reaction; (3) diastereoselective intramolecular Pauson-Khand reaction; (4) Ni-catalyzed diastereoselective conjugated 1,4-addition; and (5) radical-initiated intramolecular hydrogen atom transfer (HAT). Control experiments and density functional theory calculations support the proposed HAT process.
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