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  • Title: First asymmetric total syntheses of cernuane-type Lycopodium alkaloids, cernuine, and cermizine D.
    Author: Nishikawa Y, Kitajima M, Takayama H.
    Journal: Org Lett; 2008 May 15; 10(10):1987-90. PubMed ID: 18429621.
    Abstract:
    The first total syntheses of two cernuane-type Lycopodium alkaloids, (-)-cernuine and (+)-cermizine D, were accomplished starting from (+)-citronellal. The syntheses involved organocatalytic alpha-amination to afford oxazolidinone, which is used for diastereoselective allylation, and asymmetric transfer aminoallylation followed by stereoselective construction of an aminal moiety as key steps.
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