title: Enantioselective total synthesis of (+)-methoxystemofoline and (+)-isomethoxystemofoline.
abstract: The first enantioselective total synthesis of (+)-methoxystemofoline (2) and (+)-isomethoxystemofoline (3) has been reported. The synthesis employed the halide-assisted bromotropanonation method that we developed recently to construct the core structure, and Overman's strategy for the implementation of the butenolide moiety. Through this work, the structure of methoxystemofoline was revised as with an E-alkene, and its absolute configuration was established.
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, and Collaborative Innovation Centre of Chemistry for Energy Materials, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China. pqhuang@xmu.edu.cn.
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
authors.forename: Su-Yu
authors.initials: SY
authors.lastname: Huang
authors.forename: Long-Hui
authors.initials: LH
authors.lastname: Gao
authors.forename: Zhong-Yi
authors.initials: ZY
authors.lastname: Mao
authors.forename: Zong
authors.initials: Z
authors.lastname: Chang
authors.forename: Ai-E
authors.initials: AE
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C550038:methoxystemofoline