Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 41, Pages 10563-10568Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100985
Keywords
asymmetric catalysis; [3+2] annulation; lawsone; methanobenzo[f]azulenes; organocatalysis
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Funding
- Department of Science and Technology (DST), SERB, New Delhi [CRG/2018/000775]
- UoH-IoE grant [UoH/IoE/RC1/RC1-20-002]
- Council of Scientific and Industrial Research (CSIR), New Delhi
- University Grants Commission (UGC) - Dr. D.S. Kothari Postdoctoral Fellowship (DSKPDF) scheme, New Delhi
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By utilizing a quinine-thiourea-catalyzed sequential reaction, Lawsone aldehydes were transformed into chiral methanobenzo[f]azulenes/methanodibenzo[a,d][7]annulenes with high diastereomeric ratio and enantiomeric excess. This approach is valuable for the synthesis of important antibiotics due to the nature of the final molecules.
Lawsone aldehydes were directly transformed into the biologically important, unique carbon skeleton of chiral methanobenzo[f]azulenes/methanodibenzo[a,d][7]annulenes in high dr and ee and in very good yields by using quinine-thiourea-catalyzed tandem Wittig/intramolecular Michael/intramolecular aldol reactions. This asymmetric catalytic tandem protocol will be highly useful because these final molecules are basic skeletons of important antibiotics.
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