title: Asymmetric total synthesis of neoxaline.
abstract: A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.
authors: Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Tokyo 108-8641, Japan.
authors: Tetsuya
authors: T
authors: Ideguchi
authors: Takeshi
authors: T
authors: Yamada
authors: Tatsuya
authors: T
authors: Shirahata
authors: Tomoyasu
authors: T
authors: Hirose
authors: Akihiro
authors: A
authors: Sugawara
authors: Yoshinori
authors: Y
authors: Kobayashi
authors: Satoshi
authors: S
authors: Ōmura
authors: Toshiaki
authors: T
authors: Sunazuka
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C022264:neoxaline