title: Synthesis of (±)-Lasubine II Using N-Methoxyamines.
abstract: The synthesis of (±)-lasubine II has been achieved through a three-component allylation capitalizing on the unique properties of N-methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubine II in a single operation. The N-methoxy group was efficiently used for the subsequent nitrone formation. A single-step cyclization of isoxazolidines or N-methoxyamines to form functionalized piperidine rings was also developed.
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: Takashi
authors.initials: T
authors.lastname: Yokoyama
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: Yutaro
authors.initials: Y
authors.lastname: Fukami
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan. takaakis@applc.keio.ac.jp.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Sato
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan. chida@applc.keio.ac.jp.
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
mesh_terms: D003500:Cyclization; D006898:Hydroxylamines / Q000138:chemical synthesis / Q000737:chemistry*; D031563:Lagerstroemia / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006898:Hydroxylamines; D010880:Piperidines; D011807:Quinolizines; C414385:lasubin I; C005214:methoxyamine
keywords: allylation; amines; lasubine; multicomponent reactions; total synthesis