Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 41, Pages 14535-14539Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603664
Keywords
chiral auxiliaries; Knoevenagel condensation; Nazarov cyclization; sulfoxides; total synthesis
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Funding
- National Natural Science Foundation of China [81373276]
- Shanghai Municipal Committee of Science and Technology [14XD1400300, 13431900101]
- Specialized Research Fund for the Doctoral Program of Higher Education [20130071110070]
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The synthesis of enantiomerically pure 3-aryl substituted indanones is developed using an enantioselective sulfoxide-based Knoevenagel condensation/Nazarov cyclization procedure. After the reductive desulfonation of the methyl para-tolyl sulfoxide-containing chiral auxiliary under mild conditions, selected enantiomerically pure indanone is used for the divergent total syntheses of three resveratrol natural products (+)-isopaucifloralF, (+)-quadrangularinA, and (+)-pallidol.
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