866488-35-9

Upstream product

• 68471-58-9 1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 473436-50-9 benzyl 2,3-dihydroxy-1-piperidinecarboxylate 

Downstream Products

• 55837-20-2 (+)-halofuginone 
• 17395-31-2 (+)-halofuginone didydrobromide 
• 55837-20-2 halofuginone 
• 17395-31-2 (-)-halofuginone didydrobromide 
• 1185729-94-5 (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate 
• 24159-07-7 febrifugine 
• 1091605-50-3 (2R,3S)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester 
• 1203455-33-7 (2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester 
• 1091605-41-2 benzyl (E)-4-benzyloxycarbonyloxy-7-oxooct-5-enylcarbamate 
• 24159-07-7 dl-febrifugine 
• 312298-31-0 benzyl N-[3-(5-methyl-2-furyl)propyl]carbamate 
• 312298-32-1 benzyl N-(4,7-dioxooctyl)carbamate 

Relevant academic research and scientific papers

Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition

Intramolecular conjugate addition of γ-substituted (E)- α,β-unsaturated ketones with a Lewis acid (BF3· OEt2) selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction. Georg Thieme Verlag Stuttgart.

Concise synthesis of dl-febrifugine

Racemic compound (1) of the antimalarial agents febrifugine (d-1) was synthesized using an stereoselective Michael reaction of an ω-amidoenone (5) which was prepared by the Wittig reaction of piperidinediol (7).