title: Total synthesis of (-)-(α)-kainic acid via a diastereoselective intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone with an alkyne.
abstract: An enantioselective synthesis of (-)-(α)-kainic acid in 15 steps with an overall yield of 24% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with complete diastereoselectivity via an unprecedented SmI2-catalyzed intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone and an alkyne. Double bond isomerization was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(α)-kainic acid.
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Road Zu Chong Zhi, Zhangjiang Hi-Tech Park, Shanghai 201203, P.R. China.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Luo
authors.forename: Bing
authors.initials: B
authors.lastname: Zhou
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Li
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D061565:Cycloaddition Reaction; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D007659:Ketones; D011759:Pyrrolidines; C032519:pyrrolidine; D007608:Kainic Acid