Diazonamide Synthesis Studies: Use of Negishi Coupling to Fashion Diazonamide-Related Biaryls with Defined Axial Chirality

• DOI: 10.1021/ol026694t
• Publication Date: 2002-09-26T05:20:48Z
• Authors: Ken S. Feldman; Kyle J. Eastman; Guillaume Lessene
• Keywords: Molecular Structure; Stereoisomerism; Heterocyclic Compounds, 4 or More Rings; Oxazoles; 01 natural sciences; Catalysis; 0104 chemical sciences

The syntheses of a bis indole and an indole salicylate with the required axial chirality for diazonamide A are reported. Atropselectivity in these biaryl systems is enforced by an sp(3) stereogenic center in a lactone tether in both cases. [structure: see text]