title: Sulfoxide-Based Enantioselective Nazarov Cyclization: Divergent Syntheses of (+)-Isopaucifloral F, (+)-Quadrangularin A, and (+)-Pallidol.
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.
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, P.R. China.
authors.forename: Mei-Lin
authors.initials: ML
authors.lastname: Tang
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, P.R. China.
authors.forename: Peng
authors.initials: P
authors.lastname: Peng
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, P.R. China.
authors.forename: Zheng-Yu
authors.initials: ZY
authors.lastname: Liu
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, P.R. China.
authors.forename: Jian
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, P.R. China.
authors.forename: Jian-Ming
authors.initials: JM
authors.lastname: Yu
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, P.R. China. sunxunf@shmu.edu.cn.|Shanghai Key Laboratory of Clinical Geriatric Medicine, Shanghai, 201203, P.R. China. sunxunf@shmu.edu.cn.
authors.forename: Xun
authors.initials: X
authors.lastname: Sun
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D003500:Cyclization; D007189:Indans / Q000737:chemistry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D001688:Biological Products; D007189:Indans; D011083:Polycyclic Compounds; D013267:Stilbenes; D013454:Sulfoxides; C535072:pallidol; C487911:pauciflorol F; C000603014:quadrangularin A; C013352:indacrinone
keywords: Knoevenagel condensation; Nazarov cyclization; chiral auxiliaries; sulfoxides; total synthesis