1225377-76-3

Upstream product

• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 1225377-71-8 2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile 
• 75-77-4 chloro-trimethyl-silane 
• 1225377-78-5 (4aR,5S,10bR,12R)-1-benzyl-8-ethynyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 
• 1225377-69-4 2-((1S,2R,3R,5R)-3-ethynyl-2-(3-hydroxypropyl)-3-(benzylamino)-5-methylcyclohexyl)acetonitrile 
• 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 
• 1225377-67-2 3-((1R,2R,4R,6S)-2-(benzylamino)-6-(cyanomethyl)-2-ethynyl-4-methylcyclohexyl)propyl acetate 
• 1225377-65-0 3-((1R,2S,4R,6S)-2-acetoxy-6-(cyanomethyl)-2-ethynyl-4-methylcyclohexyl)propyl acetate 
• 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

• 1438285-71-2 C₄₆H₅₄N₄ 

Relevant academic research and scientific papers

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.