30883-62-6

Basic information

• Product Name: (-)-N-nor-protosinomenine hydrochloride
• CAS NO: 30883-62-6
• Molecular Weight: 351.83
• Mol File: 30883-62-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-N-nor-protosinomenine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-N-nor-protosinomenine hydrochloride(30883-62-6)
• EPA Substance Registry System: (-)-N-nor-protosinomenine hydrochloride(30883-62-6)

Safety Data

• Hazardous Substances Data: 30883-62-6(Hazardous Substances Data)

Upstream product

• 21416-19-3 (+/-)-O,O-dibenzyl-N-nor-protosinomenine 
• 28594-07-2 (+)-O,O-dibenzyl-N-nor-protosinomenine 
• 21416-19-3 (-)-OO-dibenzyl-N-nor-protosinomenine 

Relevant articles and documents

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

LATE STAGES IN THE BIOSYNTHESIS OF ABNORMAL ERYTHRINA ALKALOIDS

The incorporation of (+/-)-, N-norprotosinomenine, N-nor-orientaline, N-nor-reticuline, norlaudanosoline, protosinomenine, and N--2-(4-hydroxyphenyl)ethylamine into coccuvine has been studied, and the specific utilisati