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Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis



Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis



Chemistry, An Asian Journal 11(9): 1425-1435



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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Accession: 057260907

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PMID: 26991640

DOI: 10.1002/asia.201600131


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