title: Multicomponent assembly processes for the synthesis of diverse yohimbine and corynanthe alkaloid analogues.
abstract: A strategy involving a Mannich-type multicomponent assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alkaloids. Several other new multicomponent assembly processes were developed to access dihydro-β-carboline-fused benzodiazepines, pyrimidinediones, and rutaecarpine derivatives.
authors.affiliation: Department of Chemistry and Biochemistry, The Texas Institute for Drug and Diagnostic Development, The University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Brett A
authors.initials: BA
authors.lastname: Granger
authors.forename: Zhiqian
authors.initials: Z
authors.lastname: Wang
authors.forename: Kyosuke
authors.initials: K
authors.lastname: Kaneda
authors.forename: Zhenglai
authors.initials: Z
authors.lastname: Fang
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D032068:Pausinystalia; D015016:Yohimbine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D015016:Yohimbine; C030374:indole