title: Synthesis of bis(indole) alkaloids from Arundo donax: the ynindole Diels-Alder reaction, conformational chirality, and absolute stereochemistry.
abstract: Bis(indole) alkaloids from Arundo donax were synthesized using the first ynindole Diels-Alder reaction. The alkaloids are chiral, having stable enantiomeric conformations with half-lives of racemization of t1/2 = 4150-25100 seconds at room temperature. Their absolute stereochemistry was determined using the exciton chirality method.
authors.affiliation: Department of Chemistry, Oregon State University, Corvallis, OR 97331 (USA).
authors.forename: Jingjin
authors.initials: J
authors.lastname: Chen
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Ferreira
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Beaudry
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D061565:Cycloaddition Reaction; D007211:Indoles / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000480:Alkynes; D001688:Biological Products; D007211:Indoles
keywords: alkynes; chirality; cycloaddition; natural products; total synthesis