title: Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of (-)-Aspidophylline A.
abstract: The first enantioselective total synthesis of (-)-aspidophylline A, including assignment of its absolute configuration has been accomplished. A key element of the synthesis is a highly enantioselective indole allylic alkylation/iminium cyclization cascade which was developed by employing a combination of Lewis acid activation and an iridium/ligand catalyst. This strategy relies on the direct use of 2,3-disubstituted indoles with secondary allylic alcohols appended at C2 and heteronucleophiles appended at C3, indoles which are easily prepared from simple starting materials under C-H activation conditions.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei 132#, Kunming, 650201, China.
authors.forename: Shi-Zhi
authors.initials: SZ
authors.lastname: Jiang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei 132#, Kunming, 650201, China.|University of Chinese Academy of Sciences, Beijing, 100039, China.
authors.forename: Xue-Yi
authors.initials: XY
authors.lastname: Zeng
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei 132#, Kunming, 650201, China.|University of Chinese Academy of Sciences, Beijing, 100039, China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Liang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei 132#, Kunming, 650201, China.
authors.forename: Ting
authors.initials: T
authors.lastname: Lei
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei 132#, Kunming, 650201, China.
authors.forename: Kun
authors.initials: K
authors.lastname: Wei
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei 132#, Kunming, 650201, China. yangyurong@mail.kib.ac.cn.
authors.forename: Yu-Rong
authors.initials: YR
authors.lastname: Yang
keywords: cyclizations; enantioselectivity; indoles; iridium; total synthesis