Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 8, Pages 2177-2182Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100033
Keywords
Enantioselective synthesis; Tetrahydrofuranyl spirooxindole; 3-Hydroxyoxindoles; Cyclic ketolactams; Anticancer bioactivity
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Funding
- NSFC [81703809, 21871031, 21702021]
- Chengdu Talents Program
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Asymmetric construction of pharmacologically interesting tetrahydrofuranyl spirooxindole frameworks has been successfully achieved through organocatalytic reactions, with remarkable results in terms of yield and stereochemistry. The synthetic derivatives show significant anticancer activity against a panel of cancer cell lines, demonstrating their potential as therapeutic agents.
Asymmetric construction of pharmacologically interesting tetrahydrofuranyl spirooxindole frameworks has been achieved through organocatalytic [3+2] annulations of the readily available 3-hydroxyoxindoles and pyrrolidone-derived cyclic ketolactams. A variety of chiral spiro tetrahydrofuranyl products, which contain four contiguous stereocenters including two tetrasubstituted carbon centers, have been rapidly synthesized with remarkable results (up to 99% yield, >95:5 dr, and 99:1 er). Synthetic derivatization of the hemiketal moiety enables the installation of various halogen atoms into the structurally complex molecules in a stereospecific manner. Preliminary screening of anticancer bioactivity was performed, and 4 w showed obvious inhibitory capacity to the proliferation on a panel of cancer cell lines.
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