27498-04-0

Basic information

• Product Name: (13aS)-5,8,13,13aα-Tetrahydro-2,11-dimethoxy-6H-dibenzo[a,g]quinolizine-1,10-diol
• Synonyms: (13aS)-5,8,13,13aα-Tetrahydro-2,11-dimethoxy-6H-dibenzo[a,g]quinolizine-1,10-diol;Caseamine
• CAS NO: 27498-04-0
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.37434
• Mol File: 27498-04-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (13aS)-5,8,13,13aα-Tetrahydro-2,11-dimethoxy-6H-dibenzo[a,g]quinolizine-1,10-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (13aS)-5,8,13,13aα-Tetrahydro-2,11-dimethoxy-6H-dibenzo[a,g]quinolizine-1,10-diol(27498-04-0)
• EPA Substance Registry System: (13aS)-5,8,13,13aα-Tetrahydro-2,11-dimethoxy-6H-dibenzo[a,g]quinolizine-1,10-diol(27498-04-0)

Safety Data

• Hazardous Substances Data: 27498-04-0(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 

Downstream Products

• 34413-12-2 (-)-caseadine 
• 19637-57-1 (-)-O-methyl caseadine 

Relevant articles and documents

Total Synthesis of the Ortho-Hydroxylated Protoberberines (S)-Govaniadine, (S)-Caseamine, and (S)-Clarkeanidine via a Solvent-Directed Pictet-Spengler Reaction

The common para regioselectivity in Pictet-Spengler reactions with dopamine derivatives is redirected to the ortho position by a simple change of solvents. In combination with a chiral auxiliary on nitrogen, this ortho-selective Pictet-Spengler produced the 1-benzyltetrahydroisoquinoline alkaloids (S)-crassifoline and (S)-norcrassifoline and the bioactive 1,2-dioxygenated tetrahydroprotoberberine alkaloids (S)-govaniadine, (S)-caseamine, and (S)-clarkeanidine with high enantiopurity. Ortho/para ratios up to 89:19 and diastereomeric ratios up to 85:15 were obtained during formation of the B-ring. The general applicability of this solvent-directed regioselectivity was demonstrated with a second Pictet-Spengler reaction as required for C-ring formation of caseamine (o/p = 14:86 in trifluoroethanol) and clarkeanidine (o/p = 86:14 in toluene).