Affiliation:
1. University of Basel Department of Chemistry St. Johanns-Ring 19 4056 Basel Switzerland
2. University of Geneva Department of Physical Chemistry 30 Quai Ernest-Ansermet 1211 Geneva 4 Switzerland
Abstract
AbstractThe 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.
Funder
Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
Universität Basel
Subject
General Chemistry,Catalysis