1227366-20-2Relevant academic research and scientific papers
First asymmetric synthesis of boehmeriasin A
Dumoulin, David,Lebrun, Stephane,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
experimental part, p. 1943 - 1950 (2010/06/13)
The first asymmetric synthesis of phenanthroquinolizidine alkaloid (R)-boehmeriasin A is described. Two alternative synthetic pathways to the key intermediate (RS,R)-4 were achieved through a combination of highly diastereoselective 1,2-nucleophilic addition on (-)-(S)-l-amino-2-(methoxy methyl)pyrrolidine hydrazones with a ring-closing metathesis to ensure the construction of the piperidine template. A subsequent acylation/oxidation/aldol condensation/radical cyclization sequence completed the assembly of the title (R)configured natural product.
