Sulfoxide‐Based Enantioselective Nazarov Cyclization: Divergent Syntheses of (+)‐Isopaucifloral F, (+)‐Quadrangularin A,and (+)‐Pallidol |
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| Authors: | Mei‐Lin Tang Peng Peng Zheng‐Yu Liu Jian Zhang Jian‐Ming Yu Prof?Dr Xun Sun |
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| Institution: | 1. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai, P.R. China;2. Shanghai Key Laboratory of Clinical Geriatric Medicine, Shanghai, P.R. China |
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| Abstract: | 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 (+)‐isopaucifloral F, (+)‐quadrangularin A, and (+)‐pallidol. |
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| Keywords: | chiral auxiliaries Knoevenagel condensation Nazarov cyclization sulfoxides total synthesis |
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