title: Voatinggine and tabertinggine, pentacyclic indole alkaloids derived from an iboga precursor via a common cleavamine-type intermediate.
abstract: Two new indole alkaloids, voatinggine (1) and tabertinggine (2), which are characterized by previously unencountered natural product skeletons, were isolated from a Malayan Tabernaemontana species. The structures and absolute configuration of these alkaloids were determined using NMR and MS analysis, and X-ray diffraction analysis. A possible biogenetic pathway to these novel alkaloids from an iboga precursor, and via a common cleavamine-type intermediate, is presented.
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya , 50603 Kuala Lumpur, Malaysia.
authors.forename: Choy-Eng
authors.initials: CE
authors.lastname: Nge
authors.forename: Chew-Yan
authors.initials: CY
authors.lastname: Gan
authors.forename: Yun-Yee
authors.initials: YY
authors.lastname: Low
authors.forename: Noel F
authors.initials: NF
authors.lastname: Thomas
authors.forename: Toh-Seok
authors.initials: TS
authors.lastname: Kam
mesh_terms: D018360:Crystallography, X-Ray; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D013237:Stereoisomerism; D030014:Tabernaemontana / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; C558889:cleavamine; C586606:tabertinggine; C586605:voatinggine