792183-69-8

Upstream product

• 129708-94-7 (2S)-(-)-2-(4,4-dimethoxybutyl)-1-((1S)-1-phenylethyl)-pyrrolidine 
• 129708-97-0 (5R,9R)-(+)-5-cyanoindolizidine 
• 129708-96-9 (2S)-(-)-2-(4,4-dimethoxybutyl)pyrrolidine 
• 126017-85-4 N-<(S)-1'-Phenylethyl>-5-prop-2''-enylpyrrolidin-2-one 
• 177981-20-3 (6R)-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methyl-2-piperidone 
• 204845-25-0 (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 152615-80-0 (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine 
• 503843-20-7 (2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine 
• 129708-98-1 (5R,9R)-5-cyano-5-methylindolizidine 

Relevant academic research and scientific papers

Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam

Starting from a common lactam, (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1), or its enantiomer, the enantioselective synthesis of 2-alkylpiperidines and cis- and trans-2,6-dialkylpiperidines is reported. The potential of this approach is illustrated by the synthesis of the piperidine alkaloids (R)-coniine, (2R,6S)-dihydropinidine, (2R,6R)-lupetidine, and (2R,6R)-solenopsin A, the indolizidine alkaloids (5R,8aR)-indolizidine 167B and (3R,5S,8aS)-monomorine I, and the nonnatural base (4R,9aS)-4-methylquinolizidine.

Enantioselective Total Syntheses of Indolizidine Alkaloids 167B and 209D

Enantioselective total syntheses of the indolizidine alkaloids 167B and 209D are described.The sytheses proceed via a common late-stage intermediate, amino nitrile 8.Each alkaloid was prepared in 10 steps and approximately 23percent overall yield from (S)