6883-33-6

Usage

Uses

Unfortunately, the provided materials do not mention any specific applications or uses for 17-Norcuran. Further research would be required to determine its potential uses in various industries.

References

Kump et aI., Helv. Chim. Acta, 47, 1497 (1964) Synthesis: Dadson, Harley-Mason, Foster., Chem. Commun., 1233 (1968)

Upstream product

• 138040-07-0 2-Allyl-2-(2-nitrophenyl)-1,3-cyclohexanedione 
• 222162-00-7 (3aR,7aS)-3a-(2-Nitro-phenyl)-4-oxo-2,3,3a,4,7,7a-hexahydro-indole-1-carboxylic acid 1-chloro-ethyl ester 
• 192431-42-8 (3aR,7aS)-3a-(2-Nitro-phenyl)-4-oxo-octahydro-indole-1-carboxylic acid 1-chloro-ethyl ester 
• 192431-40-6 (3aR,7aS)-3a-(2-Nitro-phenyl)-1-(4-trimethylsilanyl-but-2-ynyl)-1,2,3,3a,7,7a-hexahydro-indol-4-one 
• 222162-04-1 (3aR,7aS)-3a-(2-Nitro-phenyl)-4-oxo-5-phenylselanyl-octahydro-indole-1-carboxylic acid 1-chloro-ethyl ester 
• 2912-06-3 dl-tubifoline 
• 1501-26-4 methyl 4-(chlorocarbonyl)butyrate 
• 73609-01-5 3-(2-chlorobutyryl)-7-oxo-1,2,3,4,5,6,7,8-octahydroazonino<5,4-b>indole 
• 58074-78-5 C₁₈H₂₂N₂O 
• 73554-49-1 6-oxo-(2-aminoethyl)-6,7,8,9-tetrahydropyrido<1,2-a>indole 
• 89650-71-5 [2-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-ethyl]-carbamic acid benzyl ester 
• 89650-70-4 3-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-propionyl azide 
• 73609-00-4 3-(2-chlorbutyryl)-1,2,3,4,5,6,7,8-octahydroazonino<5,4-b>indole 
• 89650-67-9 3-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-propionyl chloride 

Relevant academic research and scientific papers

(-)-Tubifolidine as strychnos indole alkaloid: Spectroscopic charactarization (FT-IR, NMR, UV-Vis), antioxidant activity, molecular docking, and DFT studies

Strychnos indole alkaloids, which include tubifolidine (2) and are an important group of complex and interesting natural compounds as bio-actives, antioxidants as well as ABCDE ring system. Four different procedures have been employed for the tubifolidine: (i) spectroscopic characterization; (ii) antioxidant activity; (iii) molecular docking, and (iv) DFT studies. The spectroscopic characterization of tubifolidine was performed by FT-IR, NMR, and UV-Vis techniques, and elemental analysis. The antioxidant activity was explored by the DPPH method and molecular docking was used to enlighten the possible interaction of the tubifolidine with the topoisomerase receptor. The DFT/B3LYP/6–311++G(df,pd) level was used for geometry optimization, structure verification and to calculate the reactivity descriptors of tubifolidine. Besides, TD-DFT/B3LYP level was used to evaluate the electronic spectra and main excitations: the results revealed that the observed peak at 292 and 254 nm were mainly associated with n→ Π* and Π→ Π* transitions, and a bit σ → Π*. Besides, the n→ Π* and Π→ Π* transitions in the ground state contributed to the lowering stability of tubifolidine. FMO analysis displayed that the electro-donating power was dominant over the electroaccepting capability of tubifolidine.

Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids

A highly enantioselective tandem Michael addition of tryptamine-derived oxindoles to alkynones was developed by taking advantage of a chiral N,N′-dioxide Sc(OTf)3 catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine-3,3′-oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(?)-tubifoline, (?)-tubifolidine, (?)-dehydrotubifoline] was achieved in 10–11 steps.

A general synthetic entry to Strychnos alkaloids of the curan type via a common 3a-(2-nitrophenyl)hexahydroindol-4-one intermediate. Total syntheses of (±)- and (-)-tubifolidine, (±)-akuammicine, (±)-19,20-dihydroakuammicine, (±)-norfluorocurarine, (±)-ec

A general strategy for the synthesis of pentacyclic Strychnos alkaloids with the curan skeleton has been developed. It utilizes 3a-(2-nitrophenyl)hexahydroindol-4-one (23), which was prepared from 2-allyl-2-(2-nitrophenyl)-1,3-cyclohexanedione (15), as th

Total syntheses of the Strychnos indole alkaloids (-)-tubifoline, (-)-tubifolidine, and (-)-19,20-dihydroakuammicine

Two different strategies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of 1-(3-pyridyl)ethanol, followed by partial reduction of the pyridine ring to the tetrahydropyridine level, Claisen rearrangement of the resulting allylic alcohol, and finally Smith indolization. Whereas 2-(4-piperidylmethyl)indole 6 could not be converted to tetracyclic ABDE substructures of Strychnas alkaloids, photocyclization of chloroacetamide 14, derived from (piperidylmethyl)indole 13, satisfactorily afforded the stemmadenine-type tetracycle 15, which was then converted to the alkaloids (-)-tubifoline, (-)-tubifolidine, and (-19,20-dihydroakuammicine.

A SYNTHETHIC ROAD TO THE FOREST OF STRYCHNOS, ASPIDOSPERMA, SCHIZOZYGANE AND EBURNAMINE ALKALOIDS BY WAY OF THE NOVEL PHOTOISOMERIZATION

The novel photoisomerization of 1-acylindoles accompanied by a conversion of indole to indolenine afforded 3-acylindolenines, a so far unknown reactive species, as a major product.This reaction was thorougly investigated and applied with success to the total synthesis of Strychnos, Aspidosperma, Schizozygane and Eburnamine alkaloids through a versatile intermediate 9-membered ring system,synthesized in a one pot reaction by photolysis and the simultaneous ring enlargement.