1225377-67-2

Upstream product

• 1225377-65-0 3-((1R,2S,4R,6S)-2-acetoxy-6-(cyanomethyl)-2-ethynyl-4-methylcyclohexyl)propyl acetate 
• 100-46-9 benzylamine 
• 101693-93-0 (5R)-5-methyl-2-(phenylthio)cyclohexan-1-one 
• 308358-04-5 (6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one 
• 89-82-7 pulegone 
• 1225377-92-3 3-((4R)-4-methyl-2-oxo-1-(phenylthio)cyclohexyl)propyl acetate 
• 1225377-63-8 3-((1R,2S,4R,6S)-6-(cyanomethyl)-2-ethynyl-2-hydroxy-4-methylcyclohexyl)propyl acetate 
• 1225377-61-6 3-((1R,2S,4R)-2-(cyanomethyl)-4-methyl-6-oxocyclohexyl)propyl acetate 
• 1225377-59-2 (R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propyl acetate 

Downstream Products

• 1225377-69-4 2-((1S,2R,3R,5R)-3-ethynyl-2-(3-hydroxypropyl)-3-(benzylamino)-5-methylcyclohexyl)acetonitrile 
• 1438285-83-6 C₄₄H₅₈N₄O₂Si 
• 1438285-84-7 C₄₄H₅₈N₄O₂Si 
• 1225377-71-8 2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile 
• 1438285-85-8 C₄₄H₅₈N₄OSi 
• 1438285-86-9 C₄₄H₅₈N₄OSi 
• 1225377-74-1 (4aR,5S,10bR,12R)-1-benzyl-12-methyl-9-(trimethylsilyl)-8-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 
• 1225377-76-3 (4aR,5S,10bR,12R)-1-benzyl-12-methyl-9-((trimethylsilyl)ethynyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 
• 1438285-38-1 (4aR,5S,10bR,12R)-1-benzyl-9-(tert-butyldimethylsilyl)-8-((tertbutyldimethylsilyl)ethynyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 
• 1438285-39-2 (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-((triisopropylsilyl)-ethynyl)-9-(trimethylsilyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 
• 1438285-40-5 C₂₉H₃₇N₃SSi 
• 1438285-42-7 C₃₀H₃₈N₂SSi 
• 1438285-44-9 (4aR,5S,10bR,12R)-1-benzyl-12-methyl-8-(thiophene-2-yl)-9-(trimethylsilyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 
• 1438285-45-0 (4aR,5S,10bR,12R)-1-benzyl-8-(furan-2-yl)-12-methyl-9-(trimethylsilyl)-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 

Relevant academic research and scientific papers

Complanadine A, a selective agonist for the Mas-related G protein-coupled receptor X2

The first biological target for the natural product complanadine A has been determined. The pseudosymmetric alkaloid functions as a selective agonist for the Mas-related G protein-coupled receptor X2 (MrgprX2), a G protein-coupled receptor that is highly expressed in neurons. Given the potential of MrgprX2 to function as a modulator of pain, complanadine A represents a new chemical probe to selectively interrogate the physiological function of MrgprX2 as well as a potential lead for the development of antihyperalgesics for the treatment of persistent pain. While complanadine A possess agonistic activity the related natural product lycodine, representing half of complanadine A, lacks activity providing a cursory description of the structural requirements for agonistic activity.

Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions

The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycodine core.

Synthesis of (+)-complanadine A, an inducer of neurotrophic factor excretion

A total synthesis of the Lycopodium alkaloid (+)-complanadine A is described. Complanadine A has been shown to induce the secretion of neurotrophic factors from 1321N1 cells, promoting the differentiation of PC-12 cells. The use of a simplifying metal mediated [2+2+2] + [2+2+2] sequence using a silyl-substituted diyne and 2 equiv of the corresponding alkyne-nitrile has provided rapid access to the natural product.