Total Synthesis of Marine Polyketide Plakortone Q
Shinnosuke Okazaki1, Kaho Senda1, Ayaka Tokuta1
1School of Pharmacy, Tokyo University of Pharmacy and Life Sciences.
Chemical & Pharmaceutical Bulletin
|February 4, 2024
Abstract:
The total synthesis of the natural bicyclo[3.3.0]furanolactone polyketide, plakortone Q, was achieved in 24 steps from (R)-Roche ester. The main feature of this synthetic strategy is the stereoselective construction of a central tetrahydrofuran moiety with four consecutive stereoisomeric centers using the Upjohn dihydroxylation of oxiranyl-substituted alkenes and acid-mediated 5-endo-tet cyclization.
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