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  • Title: Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis.
    Author: Liang XT, You L, Li YH, Yu HX, Chen JH, Yang Z.
    Journal: Chem Asian J; 2016 May 06; 11(9):1425-35. PubMed ID: 26991640.
    Abstract:
    Two independent synthetic approaches were evaluated for the final phase of the asymmetric total synthesis of propindilactone G (1). The key steps that led to the completion of the asymmetric total synthesis included: 1) an intermolecular oxidative heterocoupling reaction of enolsilanes to link the core structure to the side chain; 2) an intermolecular Wittig reaction for the formation of the α,β,γ,δ-unsaturated ester; and 3) a regio- and stereoselective OsO4 -catalyzed dihydroxylation of an α,β,γ,δ-unsaturated enone, followed by an intramolecular lactonization reaction to afford the final product. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised. Furthermore, the direct oxidative coupling strategy for ligation of the core of propindilactone G with its side chain may find application in the syntheses of other natural products and complex molecules.
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