108585-39-3

Basic information

• Product Name: (1R)-2-acetyl-9-methoxycarbonyl-9-azabicyclo<4.2.1>-2-nonene
• CAS NO: 108585-39-3
• Molecular Weight: 223.272
• Mol File: 108585-39-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R)-2-acetyl-9-methoxycarbonyl-9-azabicyclo<4.2.1>-2-nonene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-2-acetyl-9-methoxycarbonyl-9-azabicyclo<4.2.1>-2-nonene(108585-39-3)
• EPA Substance Registry System: (1R)-2-acetyl-9-methoxycarbonyl-9-azabicyclo<4.2.1>-2-nonene(108585-39-3)

Safety Data

• Hazardous Substances Data: 108585-39-3(Hazardous Substances Data)

Upstream product

• 17342-08-4 (S)-Pyroglutaminol 

Downstream Products

• 90741-54-1 (R)-1-((1S,6S)-2-Acetyl-9-aza-bicyclo[4.2.1]non-2-en-9-yl)-3,3,3-trifluoro-2-methoxy-2-phenyl-propan-1-one 
• 64285-06-9 (+/-)-Anatoxin A 

Relevant articles and documents

Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame

This paper describes the total synthesis of the naturally occurring alkaloids pinnamine (1) and anatoxin-a (2) from a common enantiomerically pure intermediate (7) easily available from pyroglutamic acid. The synthesis of enantiopure pinnamine proceeded in 10 steps and 4.8% overall yield, and the route was flexible enough to allow stereocontrolled access to a non-natural congener (5-epi-pinnamine) of the natural product. Intramolecular reaction of an N-acyl iminium ion was a key step in the synthesis of both pinnamine and anatoxin-a. However, in stark contrast to literature precedent, complete racemization was observed during the reaction of the N-acyliminium ion leading to the latter alkaloid.