482374-41-4

Upstream product

• 773837-37-9 sodium cyanide 
• 1428990-20-8 (-)-2-bromo-3-(2-((tert-butyldiphenylsiloxy)methyl)cyclohex-2-enyloxy)-4-methoxybenzaldehyde 
• 1428990-16-2 2-((tert-butyldiphenylsiloxy)methyl)cyclohex-2-enyl ethenyl carbonate 
• 1428990-15-1 2-tert-butyldiphenylsiloxymethyl-2-cyclohexenol 
• 238434-65-6 2-(hydroxymethyl)cyclohex-2-en-1-ol 
• 312920-40-4 (S)-(-)-methyl 6-(2-bromo-3-formyl-6-methoxyphenoxy)-cyclohex-1-enecarboxylate 
• 312920-36-8 methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate 
• 2973-58-2 2-bromoisovanillin 
• 865780-25-2 methyl 6-hydroxy-cyclohex-1-enecarboxylate 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 482374-40-3 [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol 
• 869369-38-0 [(S)-6-(2-Bromo-3-dimethoxymethyl-6-methoxy-phenoxy)-cyclohex-1-enyl]-acetonitrile 
• 621-59-0 isovanillin 

Downstream Products

• 357-70-0 Galantamine 
• 1668-85-5 (-)-epigalanthamine 
• 76-57-3 codeine 
• 57-27-2 MORPHIN 

Relevant academic research and scientific papers

Pd-catalyzed asymmetric allylic etherification using chiral biphenol-based diphosphinite ligands and its application for the formal total synthesis of (-)-galanthamine

A library of novel chiral biphenol-based diphosphinite (BOP) ligands was designed and created. These BOP ligands were applied to a Pd-catalyzed intermolecular allylic etherification reaction, which provided a key intermediate for the formal total synthesis of (-)-galanthamine with 97% ee in 97% yield.

Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine

An efficient divergent synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges by employing a Pd-catalyzed asymmetric allylic alkylation (AAA) to set the stereochemistry. Three generations of syntheses of galanthamine are discussed in detail with particular focus on the scope of the palladium-catalyzed AAA reactions and intramolecular Heck reactions. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.

An efficient enantioselective synthesis of (-)-galanthamine

An effective sequence: Palladium-catalyzed asymmetric allylic alkylation, Heck cyclization, and diastereoselective allylic oxidation were used in the total synthesis of (-)-galanthamine (3) in 14.8 % overall yield (from 1 and 2, Troc = 2,2,2-trichloroethoxycarbonyl) and with 96 % ee. This improved procedure provides the shortest and most efficient nonbiomimetic synthesis of the acetylcholinesterase inhibitor.