Total Synthesis of (±)-Brazilin Using [4 + 1] Palladium-Catalyzed Carbenylative Annulation
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 ge...
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Veröffentlicht in: | Journal of organic chemistry 2019-11, Vol.84 (22), p.14745-14759 |
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container_title | Journal of organic chemistry |
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creator | Arredondo, Vanessa Roa, Daniel E Gutman, Eugene S Huynh, Nancy O Van Vranken, David L |
description | 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. |
doi_str_mv | 10.1021/acs.joc.9b02343 |
format | Article |
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title | Total Synthesis of (±)-Brazilin Using [4 + 1] Palladium-Catalyzed Carbenylative Annulation |
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