title: Isolation and Asymmetric Total Synthesis of Perforanoid A.
abstract: A novel limonoid, perforanoid A, was isolated, and an asymmetric total synthesis was achieved in 10 steps. The key steps are chiral tertiary aminonaphthol mediated enantioselective alkenylation of an aldehyde to an allylic alcohol, Pd-catalyzed coupling of the allylic alcohol with vinyl ether to form the γ-lactone ring, and cyclopentenone ring formation through a Rh-catalyzed Pauson-Khand reaction. Preliminary studies show that perforanoid A is cytotoxic towards HEL, K562, and CB3 tumor cell lines.
authors.affiliation: School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong, 250012, PR China.
authors.forename: Chao
authors.initials: C
authors.lastname: Lv
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, PR China.
authors.forename: Xiaohui
authors.initials: X
authors.lastname: Yan
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Tu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, PR China.
authors.forename: Yingtong
authors.initials: Y
authors.lastname: Di
authors.affiliation: The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 550002, China.
authors.forename: Chunmao
authors.initials: C
authors.lastname: Yuan
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, PR China.
authors.forename: Xin
authors.initials: X
authors.lastname: Fang
authors.affiliation: The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 550002, China.
authors.forename: Yaacove
authors.initials: Y
authors.lastname: Ben-David
authors.affiliation: The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 550002, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Xia
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Jianxian
authors.initials: J
authors.lastname: Gong
authors.affiliation: School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong, 250012, PR China. yshen@sdu.edu.cn.
authors.forename: Yuemao
authors.initials: Y
authors.lastname: Shen
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China. zyang@pku.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, PR China. haoxj@mail.kib.ac.cn.
authors.forename: Xiaojiang
authors.initials: X
authors.lastname: Hao
keywords: Pauson-Khand reaction; asymmetric synthesis; cytotoxicity; limonoids; total synthesis