10-oxo-cylindrocarpidin, ein neues alkaloid aus .

Achenbach, Hans

doi:10.1016/s0040-4039(00)90726-3

Cited by 9 publications

(3 citation statements)

References 6 publications

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“…Common oxygenation patterns include primary alcohols (e.g., 6 ), 13 N,O -ketals (e.g., 7 and 8 ), 14,15 and oxygenation about the benzene fragment (e.g., 9–12 ). 16–19 Leuconolam ( 13 ) 20 is related to Aspidosperma alkaloids through indoline oxidative cleavage, and can undergo subsequent ring closure to furnish various aminal-containing structures (e.g., 14–16 ) 21–23 or additional rearrangement and fragmentation to give mersicarpine ( 17 ). 24 The pyrrole ring in rhazinilam ( 18 ) 25 is expected to originate from a biochemical oxidation pathway similar to that of leuconolam ( 13 ).…”

Section: Structural Overview Of Aspidosperma and Related Monoterpenmentioning

confidence: 99%

Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids

2018

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Section: Structural Overview Of Aspidosperma and Related Monoterpenmentioning

confidence: 99%

Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids

2018

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“…3c 10-Oxocylindrocarpidine 7 is a more highly oxidized alkaloid that was isolated from Tabernaemontana amygdalifolia by Achenbach. 4 Aspidospermine 8 is the prototypical member of the group. 8 was first isolated in 1878 from the bark of Aspidosperma quebracho by Fraude 5 and later from several other natural sources.…”

Section: ■ Introductionmentioning

confidence: 99%

“…From the same plant source, the same group also isolated a different alkaloid, named N -acetylcylindrocarpinol 6 , in which the angular carboxymethyl group was replaced by an angular 2-hydroxyethyl moiety . 10-Oxocylindrocarpidine 7 is a more highly oxidized alkaloid that was isolated from Tabernaemontana amygdalifolia by Achenbach . Aspidospermine 8 is the prototypical member of the group.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective and Divergent Total Synthesis of (+)-10-Oxocylindrocarpidine, (+)-Cylindrocarpidine, (−)-N-Acetylcylindrocarpinol, and (+)-Aspidospermine

Shen

Zhao

et al. 2014

J. Org. Chem.

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The catalytic enantioselective and divergent total syntheses of Aspidosperma alkaloids (+)-10-oxocylindrocarpidine 7, (+)-cylindrocarpidine 1, (-)-N-acetylcylindrocarpinol 6, and (+)-aspidospermine 8 have been accomplished in 11 steps from a common precursor (15) on the basis of a highly concise route. The route features three metal-catalyzed reactions, including the key Pd-catalyzed decarboxylative asymmetric allylation of carbazolones developed in our laboratory. Our syntheses, using a combination of C-H activation, enantioselective catalysis, and collective synthesis, represent the first total synthesis of 10-oxocylindrocarpidine and the first asymmetric total synthesis of cylindrocarpidine and N-acetylcylindrocarpinol.

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Metabolite Profiling of Anti‐Addictive Alkaloids from Four Mexican Tabernaemontana Species and the Entheogenic African Shrub Tabernanthe iboga (Apocynaceae)

Krengel

Chevalier

Dickinson

et al. 2019

Chemistry & Biodiversity

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Ibogaine and other ibogan type alkaloids present anti‐addictive effects against several drugs of abuse and occur in different species of the Apocynaceae family. In this work, we used gas chromatography‐mass spectrometry (GC/MS) and principal component analysis (PCA) in order to compare the alkaloid profiles of the root and stem barks of four Mexican Tabernaemontana species with the root bark of the entheogenic African shrub Tabernanthe iboga. PCA demonstrated that separation between species could be attributed to quantitative differences of the major alkaloids, coronaridine, ibogamine, voacangine, and ibogaine. While T. iboga mainly presented high concentrations of ibogaine, Tabernaemontana samples either showed a predominance of voacangine and ibogaine, or coronaridine and ibogamine, respectively. The results illustrate the phytochemical proximity between both genera and confirm previous suggestions that Mexican Tabernaemontana species are viable sources of anti‐addictive compounds.

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10-oxo-cylindrocarpidin, ein neues alkaloid aus .

Cited by 9 publications

References 6 publications

Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids

Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids

Catalytic Enantioselective and Divergent Total Synthesis of (+)-10-Oxocylindrocarpidine, (+)-Cylindrocarpidine, (−)-N-Acetylcylindrocarpinol, and (+)-Aspidospermine

Metabolite Profiling of Anti‐Addictive Alkaloids from Four Mexican Tabernaemontana Species and the Entheogenic African Shrub Tabernanthe iboga (Apocynaceae)

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