Subscribe to RSS
DOI: 10.1055/s-0030-1258906
Enantioselective Synthesis of Spirooxindoles Inspired by Natural Products
A. P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schürmann, H. Preut, S. Ziegler, D. Rauh, H. Waldmann*
Max-Planck-Institut für Molekulare Physiologie, Dortmund, Technische Universität Dortmund, Chemical Genomics Centre of the Max Planck Society, Dortmund and Universität Konstanz, Germany
Publication History
Publication Date:
22 November 2010 (online)
Significance
The 3,3′-pyrrolidinyl spirooxindole scaffold is present in a large number of natural alkaloids; however, a rather limited number of synthetic approaches to this class of compounds is reported. In this paper, the authors describe the first Lewis acid catalyzed asymmetric synthesis of 3,3′-pyrrolidinyl spirooxindoles via 1,3-dipolar cycloaddition of azomethine ylides to 3-arylidene- or 3-alkylideneoxindoles. All-carbon quaternary spirocenter and three tertiary centers were generated. A number of products were obtained in 50-97% yields and 84-98% ee. Compound 2 was found to influence a number of processes in BSC-1, HCT116 p53 +/+ and -/-, and HeLa cells. These observations support the importance of natural product inspired scaffolds with complex stereochemistry as rich sources of compounds with diverse bioactivity.