6393-66-4

Basic information

• Product Name: pleiocarpamine
• Synonyms: pleiocarpamine;(16S,19E)-19,20-Didehydro-1,16-cyclocorynan-17-oic acid methyl ester
• CAS NO: 6393-66-4
• Molecular Formula: C20H22N2O2
• Molecular Weight: 322.40088
• Mol File: 6393-66-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 492°C at 760 mmHg
• Flash Point: 251.3°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 8E-10mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: pleiocarpamine(CAS DataBase Reference)
• NIST Chemistry Reference: pleiocarpamine(6393-66-4)
• EPA Substance Registry System: pleiocarpamine(6393-66-4)

Safety Data

• Hazardous Substances Data: 6393-66-4(Hazardous Substances Data)

Usage

Description

Pleiocarpamine is a carboline alkaloid found in the bark of Hunteria eburnea Pichon and the roots of Pleiocarpa rnutica Benth. It exhibits unique optical activity and ultraviolet spectral characteristics, with absorption maxima at 230 and 285 nm and a specific rotation of [α]21D + 136° (c 0.74, MeOH).

Uses

Used in Pharmaceutical Industry:
Pleiocarpamine is used as a pharmaceutical compound for its potential therapeutic properties. Its unique chemical structure and biological activity make it a promising candidate for the development of new drugs and treatments.
Used in Research and Development:
Pleiocarpamine is utilized in research and development for studying its chemical properties, biological activity, and potential applications in medicine and other fields. Its unique characteristics and presence in specific plant sources provide valuable insights for scientific exploration and innovation.

References

Kump, Schmid., Helv. Chirn. Acta, 44, 1053 (1961) Bartlettetal.,l. Org. Chern., 28,2197(1963) Hesse et al., Helv. Chirn. Acta, 47,878 (1964)

InChI:InChI=1/C20H22N2O2/c1-3-12-11-21-9-8-14-13-6-4-5-7-16(13)22-18(14)17(21)10-15(12)19(22)20(23)24-2/h3-7,15,17,19H,8-11H2,1-2H3/b12-3-/t15-,17+,19+/m1/s1

Upstream product

• 32789-73-4 20E-[3S^*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine 
• 439-66-7 (Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate 
• 1309597-54-3 (Z,2R,12bS)-tert-butyl 2-[di(methoxycarbonyl)methyl]-3-ethylidene-1,2,3,4,6,7-hexahydroindolo[2,3-a]quinolizine-12(12bH)-carboxylate 
• 153-94-6 D-tryptophan 
• 180869-66-3 (2S,12bS,13R,E)-methyl 3-ethylidene-13-(hydroxymethyl)-2,3,4,6,7,12b-hexahydro-1H-2,12-methanoindolo[2,3-a]quinolizine-13-carboxylate 
• 295788-92-0 (2R,6R,12bS,E)-benzyl 3-ethylidene-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate 
• 236750-92-8 20E-[3S^*-(3α,5β,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine-5-carboxylic acid 
• 119582-47-7 tert-butyl((1-methoxybuta-1,3-dien-1-yl)oxy)dimethylsilane 

Downstream Products

• 1662688-34-7 (±)-C-mavacurine 
• 7240-76-8 C₂₀H₂₅N₂O⁽¹⁺⁾*I^(1-) 
• 66408-46-6 macrocarpamine 
• 2723-56-0 villalstonine 

Relevant articles and documents

Bioinspired Divergent Oxidative Cyclizations of Geissoschizine: Total Synthesis of (–)-17-nor-Excelsinidine, (+)-16-epi-Pleiocarpamine, (+)-16-Hydroxymethyl-Pleiocarpamine and (+)-Taberdivarine H

We report a full account of our efforts towards bioinspired oxidative cyclizations of geissochizine and analogs to mimic the biosynthesis of the mavacuran, akuammilan, and excelsinidine groups of monoterpene indole alkaloids. The construction of the A,B,C,D ring system of geissoschizine was first achieved by merging two known syntheses of this alkaloid. Modified Ma's oxidative conditions (KHMDS/I2) applied directly to geissoschizine induced formation of the N4–C16 bond encountered in the excelsinidines core. Identical conditions applied to C16-dimethylmalonate-containing N4-quaternized substrates ended in the formation of the mavacurans core (N1–C16 bond). With this unified oxidative cyclization strategy: (–)-17-nor-excelsinidine, (+)-16-epi-pleiocarpamine, (+)-16-hydroxymethyl-pleiocarpamine, 16-formyl-pleiocarpamine and (+)-taberdivarine H were synthetized. We also report a shortened total synthesis of 16-epi-pleiocarpamine compared to our preliminary communication from a C16-monoester analog. Alternatively, 17-nor-excelsinidine was synthesized via an intramolecular nucleophilic substitution of a 7-membered ring α-chlorolactam prepared from 16-desformyl-geissoschizine.

Total Syntheses of Pleiocarpamine, Normavacurine, and C-Mavacurine

The total syntheses of C-mavacurine-type indole alkaloids, (±)-pleiocarpamine, (±)-normavacurine, and (±)-C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at C16 and the N1 position in a Corynanthe-type compound that was equipped with a diazo function. For this cyclization, the N4 modification of the substrate using an amine-borane complex was indispensable to fix the molecular conformation.

Die absolute Konfiguration von Macrolin, einem Abbauproduct des Alkaloides Villalstonin

The absolute configuration of macroline (1), a degradation product of villalstonine (2), was determined.The chemical degradation of 1 gave a mixture of (-)-(20S)-20,21-hihydro-19-desoxo-macroline (9) and (-)-(20R)-20,21-dihydro-19-desoxo-macroline (10), which was related to the degradation products 9 of (+)-ajmaline (3) and 10 of (+)-isoajmaline (4) of known absolute configuration.Together with the complete relative stereochemistry of 2 the absolute configuration of 2 and of the second moiety of 2, (+)-pleiocarpamine (20), could be derived.Since the absolute configuration of the (-)-6,7-dihydroaspidospermidine moiety of (+)-pycnanthinine has been known already , the structure by Gorman et al. represents the absolute configuration of (+)-pycnanthinine.