Methylene C(sp3)−H Arylation Enables the Stereoselective Synthesis and Structure Revision of Indidene Natural Products.

Autor: Kudashev, Anton, Vergura, Stefania, Zuccarello, Marco, Bürgi, Thomas, Baudoin, Olivier
Předmět:
Zdroj: Angewandte Chemie International Edition; 1/2/2024, Vol. 63 Issue 1, p1-6, 6p
Abstrakt: The divergent synthesis of two indane polyketides of the indidene family, namely (±)‐indidene A (11 steps, 1.7 %) and (+)‐indidene C (13 steps, 1.3 %), is reported. The synthesis of the trans‐configured common indane intermediate was enabled by palladium(0)‐catalyzed methylene C(sp3)−H arylation, which was performed in both racemic and enantioselective (e.r. 99 : 1) modes. Further elaboration of this common intermediate by nickel‐catalyzed dehydrogenative coupling allowed the rapid installation of the aroyl moiety of (±)‐indidene A. In parallel, the biphenyl system of (±)‐ and (+)‐indidene C was constructed by Suzuki–Miyaura coupling. These investigations led us to revise the structures of indidenes B and C. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index