title: Total synthesis of broussonetine F: the orthoamide Overman rearrangement of an allylic diol.
abstract: A first total synthesis of broussonetine F from diethyl L-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.
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: Naoto
authors.initials: N
authors.lastname: Hama
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Aoki
authors.forename: Shohei
authors.initials: S
authors.lastname: Miwa
authors.forename: Miki
authors.initials: M
authors.lastname: Yamazaki
authors.forename: Takaaki
authors.initials: T
authors.lastname: Sato
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D031623:Broussonetia / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D011759:Pyrrolidines; D013644:Tartrates; C556641:broussonetine F; C064501:diethyl tartrate