Novel strategies for the solid phase synthesis of substituted indolines and indoles.
Using a polymer-bound selenenyl bromide resin, o-allyl and o-prenyl anilines were cycloaded to afford a series of solid-supported indoline and indole scaffolds. These scaffolds were then functionalized and cleaved via four distinct methods, namely traceless reduction, radical cyclization, radical rearrangement, and oxidative elimination, to afford 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines, respectively. A number of small combinatorial libraries of compounds reminiscent of certain designed ligands of biological interest were constructed demonstrating the potential utility of the developed methodology to chemical biology studies and the drug discovery process.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550North Torrey Pines Road, La Jolla, CA 92037, USA. kcn@scripps.edu
Roecker
A J
AJ
Hughes
Robert
R
van Summeren
Ruben
R
Pfefferkorn
Jeffrey A
JA
Winssinger
Nicolas
N
D000814:Aniline Compounds / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D015195:Drug Design; D005609:Free Radicals / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship
D000814:Aniline Compounds; D005609:Free Radicals; D007211:Indoles; C057812:indoline; C023650:aniline