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  • Title: Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine.
    Author: Lajiness JP, Jiang W, Boger DL.
    Journal: Org Lett; 2012 Apr 20; 14(8):2078-81. PubMed ID: 22480368.
    Abstract:
    Divergent total syntheses of (+)-spegazzinine (1) and (-)-aspidospermine (2) and their extensions to the synthesis of C19-epi-aspidospermine and C3-epi-spegazzinine are detailed, confirming the relative stereochemistry and establishing the absolute configuration of (+)-spegazzinine. A powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole provided the pentacyclic skeleton and all the requisite stereochemistry of the natural products in a single reaction that forms three rings, four C-C bonds, and five stereocenters.
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