158182-18-4

Basic information

• Product Name: (S-biar)-6,8-Dihydroxy-5-(4-hydroxy-5-methoxy-7-methyl-1-naphthyl)-1(R),3(R)-dimethyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: Korupensamine A; (1R,3R)-5-(4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
• CAS NO: 158182-18-4
• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.4489
• Mol File: 158182-18-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 601.7°C at 760 mmHg
• Flash Point: 317.7°C
• Density: 1.235g/cm³
• Vapor Pressure: 4.53E-15mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: (S-biar)-6,8-Dihydroxy-5-(4-hydroxy-5-methoxy-7-methyl-1-naphthyl)-1(R),3(R)-dimethyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (S-biar)-6,8-Dihydroxy-5-(4-hydroxy-5-methoxy-7-methyl-1-naphthyl)-1(R),3(R)-dimethyl-1,2,3,4-tetrahydroisoquinoline(158182-18-4)
• EPA Substance Registry System: (S-biar)-6,8-Dihydroxy-5-(4-hydroxy-5-methoxy-7-methyl-1-naphthyl)-1(R),3(R)-dimethyl-1,2,3,4-tetrahydroisoquinoline(158182-18-4)

Safety Data

• Hazardous Substances Data: 158182-18-4(Hazardous Substances Data)

Relevant articles and documents

First Atropo-Divergent Total Synthesis of the Antimalarial Korupensamines A and B by the "Lactone Method"

The stereoselective total synthesis of the antimalarial korupensamines A (1a) and B (1b) by application of the "lactone method" is described. Key steps of this first atropo-selective access to 5,8′-coupled naphthylisoquinoline alkaloids were the regioselective intramolecular coupling of ester 8 to give the configurationally labile lactone-bridged biaryl 9 and its atropisomer-selective cleavage with a variety of chiral and achiral H-nucleophiles, yielding the configurationally stable P-diol 10a or, optionally, the M-product 10b. From the axially chiral phenylisoquinolines thus obtained atropo-diastereodivergently, the authentic natural naphthylisoquinolines with the respective axial configurations, korupensamines A (1a) and B (1b), were obtained by completion of the second naphthalene ring, starting from the previous "bridgehead" C1 unit.