169304-52-3

Upstream product

• 106731-75-3 (2S)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxypentane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 606942-41-0 (4S)-tert-butyl-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)propoxy]diphenylsilane 
• 169304-50-1 (R)-1-(tert-butyldiphenylsilyloxy)-7-octen-4-ol 
• 158649-25-3 (2S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxypentane-1,2-diol 
• 51268-87-2 (4S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol 
• 169304-51-2 (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)oxazolidine-2,4-dione 

Downstream Products

• 169304-57-8 (5R,8R,8aS)-8-Benzyloxy-5-(3'-oxopropyl)oxazolo<3,4-a>piperidin-3-one 
• 169304-56-7 (5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 169304-58-9 (5S,8R,8aS)-8-Benzyloxy-5-dodec-3'-enyloxazolo<3,4-a>piperidin-3-one 

Relevant academic research and scientific papers

Enantioselective synthesis of (-)-desoxoprosopinine by radical cyclization

Reaction of the aldehyde 12 with tributyrin hydride in the presence of AIBN gave a mixture of 13 as a 2:1 mixture of 8β-ol and 8α-ol. Conversion of 14, derived from 13, to (-)-desoxoprosopinine 3 was successfully achieved.

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.