2172-71-6

Upstream product

• 98-88-4 benzoyl chloride 
• 67-56-1 methanol 
• 6949-91-3 1-benzoyl-1,2-dihydroquinoline-2-carboxylic acid amide 
• 91-22-5 quinoline 

Relevant academic research and scientific papers

Remote control of the C-3-C-4 double-bond epoxidation of a chiral 1,2-dihydroquinoline: Application to the synthesis of (-)-(r)-sumanirole (PNU-95666E)

A twelve-step synthesis of (-)-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1,2-dihydroquinoline bearing an Evans' chiral auxiliary at N-1. A twelve-step synthesis of (-)-(R)-sumanirole hydrochloride has been developed from quinoline. In the successful approach, the key reaction is a diastereoselective epoxidation of the C-3-C-4 double bond of a 1,2-dihydroquinoline bearing a chiral oxazolidinone-derived auxiliary at N-1.