64897-37-6Relevant academic research and scientific papers
Total Synthesis of (±)-Brazilin Using [4 + 1] Palladium-Catalyzed Carbenylative Annulation
Arredondo, Vanessa,Roa, Daniel E.,Gutman, Eugene S.,Huynh, Nancy O.,Van Vranken, David L.
, p. 14745 - 14759 (2019)
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.
Total Synthesis of (+/-)-4'-Demethyl-4-epipodophyllotoxin by Insertion-Cyclization
Kende, Andrew S.,King, Margaret Logan,Curran, Dennis P.
, p. 2826 - 2828 (2007/10/02)
The total synthesis of (+/-)-4'-O-demethyl-4-epipodophyllotoxin (3) is accomplished in 13 steps and 2.4percent overall yield from piperonal through the use of an "insertion-cyclization" reaction to form the aryltetralin ring system.
Total synthesis of (±)-picropodophyllone and (±)-4'-demethylpicropodophyllone
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, (2008/06/13)
Efficient total syntheses of (±)-picropodophyllone and (±)-4'-demethylpicropodophyllone are described. These compounds are intermediates in the preparation of known antineoplastic agents.
