Voatinggine and Tabertinggine, Pentacyclic Indole Alkaloids Derived from an Iboga Precursor via a Common Cleavamine-Type Intermediate

Voatinggine and Tabertinggine, Pentacyclic Indole Alkaloids Derived from an Iboga Precursor via a Common Cleavamine-Type Intermediate

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...

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Veröffentlicht in:Organic letters 2013-09, Vol.15 (18), p.4774-4777
Hauptverfasser: Nge, Choy-Eng, Gan, Chew-Yan, Low, Yun-Yee, Thomas, Noel F, Kam, Toh-Seok
Format: Artikel
Sprache:eng
Schlagworte:
Crystallography, X-Ray
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Leaves - chemistry
Stereoisomerism
Tabernaemontana - chemistry
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container_issue 18
container_start_page 4774
container_title Organic letters
container_volume 15
creator Nge, Choy-Eng
Gan, Chew-Yan
Low, Yun-Yee
Thomas, Noel F
Kam, Toh-Seok
description 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.
doi_str_mv 10.1021/ol4021404
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source ACS Publications; MEDLINE
subjects Crystallography, X-Ray
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Leaves - chemistry
Stereoisomerism
Tabernaemontana - chemistry
title Voatinggine and Tabertinggine, Pentacyclic Indole Alkaloids Derived from an Iboga Precursor via a Common Cleavamine-Type Intermediate
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