343565-24-2

Upstream product

• 251346-98-2 (3R,5S)-3-carboxyl-5-acetoxymethylpiperidine-1-carboxylic acid benzyl ester 
• 87682-62-0 (Z)-4-(trimethylsilyl)but-3-enyl 4-methylbenzene sulfonate 
• 109720-67-4 (Z)-4-(trimethylsilyl)-3-buten-1-ylamine 
• 343565-23-1 benzyl (3R,5S)-5-acetoxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate 
• 206761-38-8 (3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester 
• 206554-22-5 (3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester 

Downstream Products

• 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 
• 1026515-92-3 6-oxo-1,5,6,8,9,10-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester 
• 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 
• 343565-25-3 benzyl (3R,5S)-5-formyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate 

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.