title: Novel sequential sigmatropic rearrangements of allylic diols: application to the total synthesis of (-)-kainic acid.
abstract: Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of (-)-kainic acid.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Katsunori
authors.initials: K
authors.lastname: Kitamoto
authors.forename: Mana
authors.initials: M
authors.lastname: Sampei
authors.forename: Yasuaki
authors.initials: Y
authors.lastname: Nakayama
authors.forename: Takaaki
authors.initials: T
authors.lastname: Sato
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D007608:Kainic Acid / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D007608:Kainic Acid