34964-75-5

Usage

Occurrence

Aristotelia peduncularia yields this alkaloid.

Upstream product

• 119184-36-0 (1S,5R,7R)-6-isopropyl-8-methylene-7-<3,3-(trimethylenedioxy)-propyl>-6-azabicyclo<3.2.1>-3-octene 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 119184-56-4 (1S,5R)-6-isopropyl-8-methylene-7-(methylthio)-6-azabicyclo<3.2.1>octa-3,6-dienium iodide 
• 119184-48-4 (1S,4SR,5R,8S)-4,8-diacetoxy-6-isopropyl-6-azabicyclo<3.2.1>octan-7-one 
• 119184-49-5 (1S,5R,8S)-8-acetoxy-6-isopropyl-6-azabicyclo<3.2.1>octan-3-en-7-one 
• 111097-74-6 (1S,5R,8S)-8-hydroxy-6-isopropyl-4-vinylidene-6-azabicyclo<3.2.1>octan-7-one 
• 119184-50-8 (1S,5R,8S)-8-hydroxy-6-isopropyl-6-azabicyclo<3.2.1>oct-3-en-7-one 
• 119184-51-9 (1S,5R)-6-isopropyl-6-azabicyclo<3.2.1>oct-3-ene-7,8-dione 
• 119184-47-3 (1S,5R,8S)-4,8-Dihydroxy-6-isopropyl-6-aza-bicyclo[3.2.1]octan-7-one 
• 119184-39-3 (1S,5S,8S)-8-hydroxy-6-isopropyl-6-azabicyclo<3.2.1>octane-4,7-dione 
• 119184-55-3 (1S,5R)-6-isopropyl-8-methylene-6-azabicyclo<3.2.1>-3-octene-7-thione 
• 119184-37-1 (1S,5R)-6-isopropyl-8-methylene-6-azabicyclo<3.2.1>oct-3-en-7-one 
• 111097-68-8 (3S,4S,5RS)-5-ethoxy-4-hydroxy-1-isopropyl-3-<5-(trimethylsilyl)-3-pentynyl>-2-pyrrolidinone 

Downstream Products

• 70474-71-4 {(1R,5S)-5-[(Z)-2-(1H-Indol-3-yl)-vinyl]-6-methylene-cyclohex-2-enyl}-isopropyl-methyl-amine 

Relevant academic research and scientific papers

Synthesis of peduncularine

Peduncularine, the principal alkaloid of the Tasmanian shrub Aristotelia peduncularis, was synthesized via the radical cyclization of 7-oxabicyclo[2.2.1]hept-2-en-5-yl ketone oxime 9 forming the 6-azabicyclo[3.2.1]octane skeleton.

Synthesis and Absolute Configuration of the Aristotelia Alkaloid Peduncularine

The first synthesis of the Aristotelia alkaloid peduncularine (1) is described.The synthetic sequence commences with (S)-malic acid and amounts to 16 steps.Key transformations are (1) the stereoselective transalkylation of the β-hydroxylactam dianion deri