169304-58-9

Upstream product

• 60902-45-6 nonyltriphenylphosphonium bromide 
• 169304-57-8 (5R,8R,8aS)-8-Benzyloxy-5-(3'-oxopropyl)oxazolo<3,4-a>piperidin-3-one 
• 169304-54-5 (S)-3-(1-Oxooct-7-en-4-yl)-2,3-dihydrooxazol-2-one 
• 169304-53-4 (S)-3-(1-Hydroxyoct-7-en-4-yl)-2,3-dihydrooxazol-2-one 
• 169304-50-1 (R)-1-(tert-butyldiphenylsilyloxy)-7-octen-4-ol 
• 169304-52-3 (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)-2,3-dihydrooxazol-2-one 
• 169304-51-2 (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)oxazolidine-2,4-dione 
• 169304-56-7 (5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 693-58-3 1-Bromononane 

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.