595-05-1

Usage

Uses

Used in Pharmaceutical Industry:
CALYCANTHINE is used as a pharmaceutical compound for its potential therapeutic properties. The alkaloid is being studied for its possible applications in the treatment of various health conditions due to its unique chemical structure and properties.
Used in Research and Development:
CALYCANTHINE is used as a research compound for further investigation into its chemical properties, potential interactions with biological systems, and possible applications in drug development. Its isolation from Palicourea alpina provides a valuable resource for scientists to explore its potential benefits and drawbacks.
Used in Traditional Medicine:
CALYCANTHINE may be used as a component in traditional medicine practices, where it could be utilized for its potential therapeutic effects. The plant family Calycanthaceae, from which it is derived, has a history of use in traditional medicine, and CALYCANTHINE could be further explored for its potential contributions to these practices.

References

Woo-Ming, Stuart, Phytochem., 14,2529 (1975)

InChI:InChI=1/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21-,22-/m1/s1

Upstream product

• 476-34-6 isoindigo 
• 91-56-5 indole-2,3-dione 
• 1380315-89-8 C₃₃H₄₂N₄O₆ 
• 1380315-86-5 (3R,3'R)-di-tert-butyl,3'-bis(2-(methoxycarbonylamino)ethyl)-2,2'-dioxo-3,3'-biindoline-1,1'-dicarboxylate 
• 1380315-87-6 (3R,3'R)-di-tert-butyl 3,3'-bis(2-nitroethyl)-2,2'-dioxo-3,3'-biindoline-1,1'-dicarboxylate 
• 1392467-98-9 C₂₈H₃₁N₃O₈ 
• 1380315-88-7 di-tert-butyl 2,2′-dioxo-[3,3′-biindoline]-1,1′-dicarboxylate 
• 59-48-3 2-oxoindole 
• 4147-36-8 (+)-Chimonanthine 
• 247061-32-1 (4S,5S)-4,5-Bis-benzyloxy-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide] 
• 247061-38-7 (3aS,7aS)-2,2-Dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5,6-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide] 
• 247061-33-2 (4S,5S)-4,5-Dihydroxy-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide] 

Downstream Products

• 218-30-4 dibenzo[c,h][2,6]naphthyridine 

Relevant academic research and scientific papers

Total Synthesis of (-)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization

Dimeric cyclotryptamine alkaloids typically feature vicinal all-carbon quaternary stereocenters and four nitrogen atoms. In comparison with the actual biosynthetic tryptophan derivatives, we designed the 2N-featured monomer 7, aiming to construct vicinal all-carbon quaternary stereocenters via a one-step dimerization process to access the 4N-featured isomeric members of this family. In this work, we disclose the first synthetic route to access the skeleton of (-)-isocalycanthine, featuring an iron-catalyzed oxidative dimerization reaction in a catalytic single-step operation with an overwhelming control of the absolute and relative stereochemistry. This strategy has been successfully applied to the total synthesis of (-)-calycanthine and 16 isocalycanthine derivatives, which demonstrates a new synthetic pathway for dimeric cyclotryptamine alkaloids.

Copper catalyzed sequential arylation-oxidative dimerization of o-haloanilides: synthesis of dimeric HPI alkaloids

In this communication, we report a copper catalyzed sequential arylation-oxidative dimerization reaction as the key step for the synthesis of hexahydropyrroloindole alkaloids (+)-chimonanthine, (+)-folicanthine and (-)-calycanthine.

Catalytic asymmetric total synthesis of chimonanthine, folicanthine, and calycanthine through double michael reaction of bisoxindole

Direct access: Sterically hindered vicinal quaternary carbon stereocenters were constructed by catalytic enantio- and diastereoselective double Michael reaction, providing straightforward access to dimeric hexahydropyrroloindole alkaloids. A Mn(4-fluorobenzoate)2/Schiff base complex and a Mg(OAc)2/benzoic acid system were used as catalysts. Copyright

Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine

Conjoined twins: An efficient and convergent strategy for the synthesis of the dimeric hexahydropyrroloindole alkaloids, (+)-chimonanthine, (+)-folicanthine, and (-)-calycanthine, is described. The simultaneous formation of the vicinal quaternary stereocenters by using a reductive dimerization reaction provides an access to the optically active key intermediate on a gram scale. (Chemical Equation Presented).