206554-22-5

Upstream product

• 1221818-73-0 (3S,5R)-Piperidine-1,3,5-tricarboxylic acid benzyl ester dimethyl ester 
• 206761-38-8 (3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester 
• 206554-33-8 (3S,5R)-3,5-Bis-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 

Downstream Products

• 251346-98-2 (3R,5S)-3-carboxyl-5-acetoxymethylpiperidine-1-carboxylic acid benzyl ester 
• 343565-23-1 benzyl (3R,5S)-5-acetoxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate 
• 343565-24-2 benzyl (3R,5S)-5-hydroxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate 
• 343565-26-4 benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)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 
• 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 
• 475301-86-1 (1S,5R,11aR)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a]-[1,5]diazocine 
• 475301-86-1 (+)-sparteine surrogate 

Relevant academic research and scientific papers

METHOD OF PRODUCING ALDEHYDE COMPOUND OR KETONE COMPOUND

A method of producing an aldehyde compound or a ketone compound by oxidation of a primary or secondary alcohol compound having, in the molecule, a group selected from an amino group, an azido group, a hydroxy group, and a hydroxy group protected with a protective group, the method containing the steps of: a first step including colliding and mixing the alcohol compound, a dialkyl sulfoxide having 2 to 8 carbon atoms, and an acid anhydride having 4 to 10 carbon atoms in a flow-through type reactor to cause a reaction; anda second step including colliding and mixing, in a flow-through type reactor, a trialkylamine having 3 to 10 carbon atoms and the mixture liquid obtained in the first step to cause a reaction; wherein the reactions in the first step and the second step are sequentially performed.

Total Enantioselective Synthesis of (-)-Cytisine

(Equation presented) The first total enantiosynthesis of the biologically active alkaloid (-)-cytisine is reported, featuring a ruthenium-catalyzed RCM reaction as the key step. The approach relies on readily available cis-piperidine-3,5-dimethanol monoacetate as the chiral building block, and it is suited for achieving the target compound in both enantiomeric forms.

Synthesis of enantiopure diamine ligands related to sparteine, via scandium triflate-catalyzed imino Diels-Alder reactions

Imino Diels-Alder reactions have been investigated as a new route to sparteine analogues. The first enantioselective synthesis of two diastereoisomeric tricyclic diamines, structurally equivalent to the ABC and BCD rings of the naturally occurring alkaloid, is reported, starting from enantiopure intermediates. The effectiveness of the diamines in the lithiation of N-Boc-pyrrolidine is discussed.

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.