title: Enantioselective total synthesis of (+)-azimine and (+)-carpaine.
abstract: [reaction: see text] The enantioselective total syntheses of (+)-azimine and (+)-carpaine have been developed, starting with (S)-1,2,4-butanetriol as a single source of chirality. The key common feature in these syntheses involves stereoselective intramolecular hetero-Diels-Alder reaction of an acylnitroso compound. The critical macrocyclic dilactonization of the N-Cbz derivatives of azimic acid and carpamic acid was efficiently achieved by using the Yamguchi macrocyclization conditions.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy & Life Science, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Taro
authors.initials: T
authors.lastname: Sato
authors.forename: Sakae
authors.initials: S
authors.lastname: Aoyagi
authors.forename: Chihiro
authors.initials: C
authors.lastname: Kibayashi