Journal
CHEMICAL COMMUNICATIONS
Volume 58, Issue 24, Pages 3929-3932Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc01008a
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Funding
- SERB [STR/2020/000061, CRG/2019/000113]
- INSPIRE, UGC
- CSIR
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A new synthesis method has been developed for the preparation of enantioenriched compounds with all-carbon quaternary stereogenic centers. The method has been successfully applied in the total synthesis of several important alkaloids.
Naturally occurring bis(cyclotryptamine) alkaloids feature vicinal all-carbon quaternary stereocenters with an elongated labile C-3a-C-3a ' Sigma bond with impressive biological activities. In this report, we have developed a thio-urea catalyzed one-pot sequential Michael addition of bis-oxindole onto selenone to access enantioenriched dimeric 2-oxindoles with vicinal quaternary stereogenic centers at the pseudobenzylic position (up to 96% ee and >20 : 1 dr). This strategy has been successfully applied for the total syntheses of either enantiomers of chimonanthine, folicanthine, and calycanthine.
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