title: Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine.
abstract: We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2'-bis-tryptamine.
authors.affiliation: Department of Biochemistry, Division of Chemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.
authors.forename: Xiangbing
authors.initials: X
authors.lastname: Qi
authors.forename: Hongli
authors.initials: H
authors.lastname: Bao
authors.forename: Uttam K
authors.initials: UK
authors.lastname: Tambar
mesh_terms: D001688:Biological Products / Q000378:metabolism; D032701:Biomimetics / Q000379:methods*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D001688:Biological Products; D026121:Indole Alkaloids; D014363:Tryptamines; C551377:trigonoliimine C; C030820:tryptamine