492-87-5

Usage

Uses

1. Used in Pharmaceutical Industry:
Julocrotine is used as a pharmaceutical compound for its potential therapeutic applications. The alkaloid's unique chemical properties and biological activities make it a valuable candidate for the development of new drugs and treatments.
2. Used in Chemical Research:
In the field of chemical research, Julocrotine serves as a subject for studying the properties and behavior of piperidinedione alkaloids. This can contribute to the understanding of their structure-activity relationships and potential applications in various industries.
3. Used in Natural Product Extraction:
Julocrotine can be utilized in the extraction and purification processes of natural products derived from plant sources, such as the roots of Juicroton montevildenisis L. This application can help in the development of new methods for obtaining bioactive compounds from natural sources.
4. Used in Drug Synthesis:
The unique structure of Julocrotine makes it a potential starting material for the synthesis of new drugs and pharmaceutical compounds. Its chemical properties can be exploited to create novel molecules with improved therapeutic effects and reduced side effects.

References

Nakano et ai., J. Org. Chem., 26, 1184 (1961)

InChI:InChI=1/C18H24N2O3/c1-3-13(2)17(22)19-15-9-10-16(21)20(18(15)23)12-11-14-7-5-4-6-8-14/h4-8,13,15H,3,9-12H2,1-2H3,(H,19,22)

Upstream product

• 22785-43-9 (S)-benzyl (2,6-dioxopiperidin-3-yl)carbamate 
• 2650-64-8 Cbz-L-Gln 
• 1304774-09-1 phenylmethyl (3S)-[2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]carbamate 
• 151367-92-9 L-tert-butyl N-[2,6-dioxohexahydro-3-pyridinyl] Carbamate 
• 13726-85-7 Boc-Gln-OH 
• 1341218-06-1 tert-butyl (S)-2,6-dioxo-1-phenethylpiperidin-3-ylcarbamate 
• 1175950-31-8 C₁₃H₁₆N₂O₂ 
• 84131-91-9 (S)-(+)-2-methylbutyric anhydride 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 121426-39-9 methyl (4S)-5-oxo-4-[[(phenylmethoxy)carbonyl]amino]-5-[(2-phenylethyl)amino]pentanoate 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 56-86-0 L-glutamic acid 
• 1304774-08-0 (4S)-5-oxo-4-[[(phenylmethoxy)carbonyl]amino]-5-[(2-phenylethyl)amino]pentanoic acid 
• 1730-91-2 (S)-2-Methylbutyric acid 

Downstream Products

• 497-80-3 N²-((S)-2-methyl-butyryl)-N¹-phenethyl-L-isoglutamine 
• 109560-60-3 N-((S)-2-methyl-butyryl)-L-glutamic acid-1-methyl ester-5-phenethylamide 

Relevant academic research and scientific papers

Glutarimide Alkaloids Through Multicomponent Reaction Chemistry

A concise four step synthetic route for glutarimide alkaloids of high biological interest is presented. The scaffold is accessed via an Ugi four component reaction, hereby introducing two points of variation. This is followed by a hydrolysis, a cyclization under mild conditions, and an amine deprotection. The diastereomers of the cyclized intermediate can be easily separated, thus leading to optically pure alkaloids. By this route, four natural products and ten derivatives were synthesized. The scope and limitations of the synthetic methodology were investigated.

Synthesis of N -[(3 S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2 S)-2-methylbutanamide (( - )-julocrotine)

The total synthesis of ( - )-julocrotine (1) starting from l-glutamic acid in 41% overall yield is described. The methodology utilizes protection, deprotection, and regioselection (carbonyl differentiation via oxazolidinone) protocols, and glutarimide ring formation is the key step.

Synthesis of (-)-julocrotine and a diversity oriented Ugi-approach to analogues and probes

An improved total synthesis of (-)-julocrotine in three steps from Cbz-glutamine, in 51% overall yield, is presented. To demonstrate the potential of the heterocyclic moiety for diversity oriented synthesis, a series of (-)-julocrotine analogues was synthesized by employing the heterocyclic precursor as an amino input in Ugi four-component reactions (Ugi-4CR) [1].

Enantioselective synthesis of glutarimide alkaloids cordiarimides A, B, crotonimides A, B, and julocrotine

Five glutarimide alkaloids cordiarimide A (5), cordiarimide B (6), crotonimide A (3), crotonimide B (4), and julocrotine (2) have been synthesized starting from Boc-L-glutamine (7). The benzylic alcohol chiral centre of cordiarimides B (6) has been established in 6:1 diastereoselectivity by catalytic asymmetric hydrogenation using Zhou's catalytic system Pd(CF 3CO2)2/(R,R)-Me-DuPhos. Copyright