title: Total synthesis of hydroxy-α- and hydroxy-β-sanshool using Suzuki-Miyaura coupling.
abstract: Here, we describe the first total synthesis of hydroxyl-α- and hydroxyl-β-sanshool, which involves Suzuki-Miyaura coupling (SMC). Hydroxy-α-sanshool (1) was synthesized by SMC of bromoalkyne 4 with boronate 3 followed by (Z)-selective reduction of the triple bond in the coupling product. Hydroxy-β-sanshool (2) was synthesized by regio- and (E)-selective conversion of 4 to iodoalkene 11 followed by SMC with 3.
authors.affiliation: Kampo Formulations Development Center, Tsumura & Co., 3586 Yoshiwara, Ami-mach, Inashiki-gun, Ibaraki 300-1192, Japan. igarashi_yasushi@mail.tsumura.co.jp
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Igarashi
authors.forename: Katsuyuki
authors.initials: K
authors.lastname: Aoki
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Nishimura
authors.forename: Isao
authors.initials: I
authors.lastname: Morishita
authors.forename: Kimitoshi
authors.initials: K
authors.lastname: Usui
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
chemical_list: D000577:Amides; C100574:sanshool