Sulfoxide‐Based Enantioselective Nazarov Cyclization: Divergent Syntheses of (+)‐Isopaucifloral F, (+)‐Quadrangularin A, and (+)‐Pallidol

作者：Mei‐Lin Tang, Peng Peng, Zhengyu Liu, Jian Zhang, Jianming Yu, Xun Sun · 发表于：Chemistry - A European Journal · 年份：2016 · DOI：10.1002/chem.201603664 · 被引用次数：50 · 研究领域：Alkaloids: synthesis and pharmacology、Traditional and Medicinal Uses of Annonaceae、Chemical synthesis and alkaloids

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.