title: The four-step total synthesis of (-)-chaetominine.
abstract: The total synthesis of the alkaloid (-)-chaetominine (1) has been achieved in four steps with an overall yield of 33.4%. Key features of our strategy include a one-pot cascade indole epoxidation - epoxide ring-opening cyclization - lactamization reaction sequence, and the use of a nitro group as a latent amino group for the one-pot construction of the quinazolinone ring. This constitutes a step economical, redox economical and protecting group-free total synthesis.
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry & Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China. pqhuang@xmu.edu.cn.
authors.forename: Qi-Long
authors.initials: QL
authors.lastname: Peng
authors.forename: Shi-Peng
authors.initials: SP
authors.lastname: Luo
authors.forename: Xiao-Er
authors.initials: XE
authors.lastname: Xia
authors.forename: Liang-Xian
authors.initials: LX
authors.lastname: Liu
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C522312:chaetominine