159142-17-3

Upstream product

• 116996-52-2 (2S)-4-O-(tert-butyldiphenylsilyl)butane-1,2,4-triol 
• 100-39-0 benzyl bromide 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 146028-83-3 (2S)-1,2-O-isopropylidene-4-(tert-butyldiphenylsilyl)butane-1,2,4-triol 

Downstream Products

• 159142-18-4 (R)-3-(1-Benzyloxy-4-tert-butyldiphenylsilyloxybutan-2-yl)-oxazolidine-2,4-dione 
• 159247-17-3 (5R,7R,7aS)-5-Benzyloxymethyl-7-hydroxytetrahydropyrrolo<1,2-c>oxazol-3-one 
• 159142-19-5 (R)-3-(1-Benzyloxy-4-tert-butyldiphenylsilyloxybutan-2-yl)-2,3-dihydrooxazol-2-one 
• 159142-24-2 (5R,7R,7aS)-5-Benzyloxymethyl-7-tert-butyldimethylsilyloxytetrahydropyrrolo<1,2-c>oxazol-3-one 
• 159142-21-9 (R)-3-(1-Benzyloxy-4-oxobutan-2-yl)-2,3-dihydrooxazol-2-one 
• 159142-20-8 (R)-3-(1-Benzyloxy-4-hydroxybutan-2-yl)-2,3-dihydrooxazol-2-one 
• 188442-97-9 (E)-3-((S)-1-Benzyloxymethyl-3-bromo-propoxy)-acrylic acid methyl ester 
• 188442-86-6 (S)-1-benzyloxy-2-tetrahydropyranyloxybutan-4-ol 
• 188442-92-4 (S)-4-bromo-1-benzyloxybutan-2-ol 
• 188442-89-9 [(S)-4-Benzyloxy-3-(tetrahydro-pyran-2-yloxy)-butoxy]-tert-butyl-diphenyl-silane 

Relevant academic research and scientific papers

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.

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.