title: Biomimetic synthesis and studies toward enantioselective synthesis of flindersial alkaloids.
abstract: A strategy allowing both stereocontrol and control over structural isomer formation has been defined for the antimalarial flindersial alkaloids. The recently reported flinderoles were demonstrated to be derived from the natural product borrerine. The structural isomers of flinderoles, the borreverines, were also produced in vitro along with the flinderoles through the dimerization of borrerine in acidic conditions. This result is thought to replicate the biosynthesis of these compounds. Flinderoles A, B, and C, desmethylflinderole C, isoborreverine, and dimethylisoborreverine can each be synthesized in three steps from tryptamine. Furthermore, progress toward a concise enantioselective synthesis of flinderoles A, B, and C is described. This work includes enantioselective conjugate addition to an unprotected indole-appended enone.
authors.affiliation: Department of Chemistry, University of Houston, 136 Fleming Building, Houston, TX, 77204-5003, USA.
authors.forename: Ravikrishna
authors.initials: R
authors.lastname: Vallakati
authors.forename: Brian J
authors.initials: BJ
authors.lastname: Lundy
authors.forename: Santa
authors.initials: S
authors.lastname: Jansone-Popova
authors.forename: Jeremy A
authors.initials: JA
authors.lastname: May
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; C538846:flinderole A
keywords: BINOL; biosynthesis; borrerine; conjugate addition; malaria