title: A short scalable route to (-)-α-kainic acid using Pt-catalyzed direct allylic amination.
abstract: An increased supply of scarce or inaccessible natural products is essential for the development of more sophisticated pharmaceutical agents and biological tools, and thus the development of atom-economical, step-economical and scalable processes to access these natural products is in high demand. Herein we report the development of a short, scalable total synthesis of (-)-α-kainic acid, a useful compound in neuropharmacology that is, however, limited in supply from natural resources. The synthesis features sequential platinum-catalyzed direct allylic aminations and thermal ene-cyclization, enabling the gram-scale synthesis of (-)-α-kainic acid in six steps and 34% overall yield.
authors.affiliation: Graduate School of Pharmaceutical Science, Kyushu University, 3-1-1 Maidashi Higashi-ku, Fukuoka 812-8582 (Japan) http://green.phar.kyushu-u.ac.jp.
authors.forename: Ming
authors.initials: M
authors.lastname: Zhang
authors.forename: Kenji
authors.initials: K
authors.lastname: Watanabe
authors.forename: Masafumi
authors.initials: M
authors.lastname: Tsukamoto
authors.forename: Ryozo
authors.initials: R
authors.lastname: Shibuya
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Morimoto
authors.forename: Takashi
authors.initials: T
authors.lastname: Ohshima
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D010984:Platinum; D007608:Kainic Acid
keywords: allylic amination; amino acids; homogeneous catalysis; platinum; total synthesis