title: Total synthesis and confirmation of the revised structures of jiangrines A, C and D.
abstract: Our previous total synthesis of the proposed structures of jiangrines C and D shows that the characteristic data of synthetic samples did not match those of the natural ones, prompting us to revise their structures. Accordingly, we now accomplished the total synthesis of jiangrines A, C and D, which confirms our deduction that their molecular skeletons should compose of 2,3-disubstituted pyrrole instead of 2,5-disubstituted pyrrole. Our current synthesis features a silver-catalyzed [3 + 2] cycloaddition between a terminal alkyne and isocyanide, and was completed concisely in only seven linear steps.
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China. chembliu@scu.edu.cn.
authors.forename: Zhijiang
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China. chembliu@scu.edu.cn and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China.
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry; D061565:Cycloaddition Reaction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D003486:Cyanides; D011758:Pyrroles; C000595479:jiangrine A; C000626188:jiangrine C; C000626189:jiangrine D; D012834:Silver