159142-23-1

Downstream Products

• 159142-24-2 (5R,7R,7aS)-5-Benzyloxymethyl-7-tert-butyldimethylsilyloxytetrahydropyrrolo<1,2-c>oxazol-3-one 
• 159247-18-4 (+)-bulgecinine 
• 159247-17-3 (5R,7R,7aS)-5-Benzyloxymethyl-7-hydroxytetrahydropyrrolo<1,2-c>oxazol-3-one 

Relevant academic research and scientific papers

A New Route to Chiral Pyrrolidines via Radical Cyclisation; Enantioselective Synthesis of (+)-Bulgecinine

Reaction of the aldehyde 11 with tributyltin hydride in the presence of AIBN gave a mixture of 12 and 13, which successfully led to (+)-bulgecinine 3.

Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (-)-desoxoprosopinine

Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin-2-ones as a diastereoisomeric mixture of 7α-ol 18 and 7β-ol 19 (2:1), with high diastereoselectivity with respect to the 5,7a positions. (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2:1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.