Journal of Organic Chemistry p. 14745 - 14759 (2019)
Update date:2022-08-05
Topics:
Arredondo, Vanessa
Roa, Daniel E.
Gutman, Eugene S.
Huynh, Nancy O.
Van Vranken, David L.
Palladium-catalyzed carbene insertion was utilized in a formal synthesis of (±)-picropodophyllone and a total synthesis of (±)-brazilin. All prior syntheses of brazilin have involved a Friedel-Crafts alkylation in the key carbon-carbon bond forming events. The palladium-catalyzed [4 + 1] reaction generates a 1-arylindane with all of the functionalities needed for formation of the indano[2,1-c]chroman ring system of brazilin. The synthesis of (±)-brazilin was achieved in 11 steps (longest linear sequence) with an overall 11% yield.
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