title: Efficient syntheses of korupensamines A, B and michellamine B by asymmetric Suzuki-Miyaura coupling reactions.
abstract: Efficient asymmetric Suzuki-Miyaura coupling reactions are employed for the first time in total syntheses of chiral biaryl natural products korupensamine A and B in combination with an effective diastereoselective hydrogenation, allowing ultimately a concise and stereoselective synthesis of michellamine B. Chiral monophosphorus ligands L1-3 are effective for the syntheses of a series of functionalized chiral biaryls by asymmetric Suzuki-Miyaura coupling reactions in excellent yields and enantioselectivities (up to 99% ee). The presence of a polar-π interaction between the highly polarized BOP group and the extended π system of arylboronic acid coupling partner is believed to be important for the high enantioselectivity.
authors.affiliation: State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.
authors.forename: Guangqing
authors.initials: G
authors.lastname: Xu
authors.forename: Wenzhen
authors.initials: W
authors.lastname: Fu
authors.forename: Guodu
authors.initials: G
authors.lastname: Liu
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
authors.forename: Wenjun
authors.initials: W
authors.lastname: Tang
mesh_terms: D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007546:Isoquinolines; D009281:Naphthalenes; C110657:korupensamine A; C072235:michellamine A