251346-98-2

Upstream product

• 206554-22-5 (3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester 
• 206761-38-8 (3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester 

Downstream Products

• 343565-26-4 benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate 
• 343565-23-1 benzyl (3R,5S)-5-acetoxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate 
• 251346-99-3 (3R,5S)-3-carboxyamido-5-acetoxymethylpiperidine-1-carboxylic acid benzyl ester 
• 251346-89-1 (1R,4R,5S)-2-oxo-4-hydroxy-7-benzyloxycarbonyl-3,7-diazabicyclo[3.3.1]nonane 
• 251347-00-9 (3R,5S)-3-carboxyamido-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester 
• 343565-24-2 benzyl (3R,5S)-5-hydroxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate 
• 343565-19-5 (1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one 
• 343565-25-3 benzyl (3R,5S)-5-formyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate 
• 343565-22-0 (1S,5R,11aS)-6,10-Dioxo-octahydro-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester 
• 343565-20-8 (1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-3,7-diazabicyclo[3.3.1]nonan-2-one 
• 343565-27-5 benzyl (3R,5S)-3-(3-butynylcarbamoyl)-5-(hydroxymethyl)piperidine-1-carboxylate 
• 343565-28-6 benzyl (3R,5S)-3-[(3-butynyl)carbamoyl]-5-formylpiperidine-1-carboxylate 
• 343565-21-9 6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

An efficient enantioselective entry to the piperidino-quinolizidine ring system of lupine alkaloids by means of n-acyliminium ion initiated cyclization reactions

An efficient methodology for the enantioselective synthesis of the decahydro-1,5-methano-pyrido[1,2-α][1,5]diazocine skeleton found in tricyclic lupine alkaloids is described, starting from 3,5-disubstituted piperidines as chiral building blocks. Alkyne- or vinylsilane-terminated N-acyliminium ion cyclizations performed on appropriate 3,7-diazabicyclo[3.3.1]nonane derivatives allow for the highly stereoselective construction of piperidino-quinolizidine ring systems. A preliminary application of this methodology results in the synthesis of the quinolizidine alkaloid virgilidone.

An efficient chemoenzymatic access to chiral 3,7- diazabicyclo[3.3.1]nonane derivatives

Enantiopure 3,7-diazabicyclo[3.3.1]nonane derivatives 4 and 5, potential precursors of quinolizidine alkaloids, were synthesised in high yields, starting from the biocatalytic asymmetrization of σ-symmetric 3,5- disubstituted piperidines. Their applicatio