Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 10, Pages 2648-2663Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001472
Keywords
Squaramide catalyst; Spiro compound; One-pot synthesis; Green oxidant; Wnt signaling inhibitory activity
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Funding
- JSPS KAKENHI [JP18 K14221, JP18KK0154]
- JST CREST [JPMJCR20R1]
- Iketani Science and Technology Foundation
- Research Foundation for Opto-Science and Technology
- Daiichi Sankyo Foundation of Life
- Hoansha Foundation
- Iwatani foundation
- AIRC
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A stereoselective synthetic route to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines was successfully achieved by an enantioselective organocatalyzed Pictet-Spengler reaction followed by a diastereoselective oxidative rearrangement. The prepared enantioenriched spiro compounds demonstrated moderate activities in a Wnt signaling inhibitory assay. Eco-friendly oxidants were used in the process, enabling rapid access to the chiral compounds.
A stereoselective synthetic route to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines was accomplished by an enantioselective organocatalyzed Pictet-Spengler reaction of tryptamines and isotryptamines followed by a diastereoselective oxidative rearrangement using eco-friendly oxidants (i. e., NaOCl . 5H(2)O and Oxone (R)). This sequential reaction enables rapid access to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines in a one-pot process. A Wnt signaling inhibitory assay of the prepared enantioenriched spiro compounds demonstrated that they exhibited moderate activities.
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