132621-84-2

Upstream product

• 179536-74-4 ethyl (4aS,6R,8aR)-(+)-hexahydro-2,2-dimethyl-5-(phenylmethyl)-4H-1,3-dioxino-[5,4-b]pyridine-6-but-(2E)-enoate 
• 179536-73-3 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol 
• 1053244-37-3 (3R,4S,6S,9aS)-6-Benzenesulfonylmethyl-4-hydroxymethyl-octahydro-quinolizin-3-ol 
• 179536-79-9 (3R,4S,6S,9aS)-(-)-{[(2,2-dimethyl)diphenylsiloxy]methyl}-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)octahydro-2H-quinolizine 
• 179536-78-8 (3R,4S,6S,9aS)-(-)-4-{[(2,2-dimethylethyl)diphenylsiloxy]methyl}-3-hydroxy-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine 
• 179536-77-7 (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene 
• 179536-80-2 (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine 
• 179536-81-3 (3R,4S,6S,9aS)-(+)-4-(iodomethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine 
• 179536-82-4 (3R,4S,6S,9aS)-(-)-3-(methoxymethoxy)-4-methyl-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine 
• 179536-83-5 (3R,4S,6S,9aS)-(-)-6-(deca-1,3-dienyl)-3-(methoxymethoxy)-4-methyloctahydro-2H-quinolizine 

Downstream Products

• 132621-83-1 (-)-clavepictine A 

Relevant academic research and scientific papers

Total synthesis of clavepictines A and B and pictamine

A short route for assembling clavepictines A and B and pictamine is described, which features elaboration of its trisubstituted piperidine moiety via condensation of a β-keto sulfone with an L-alanine-derived bromide and subsequent alkylative cyclization and construction of its quinolizidine skeleton via a diastereoselective intramolecular conjugate addition. The possible stereochemical course for this conjugate addition is discussed.

Highly stereoselective construction of 4,6-cis-substituted quinolizidine ring core: An application to enantioselective total synthesis of the marine alkaloid clavepictines A, B and pictamine

The enantioselective total synthesis of the marine alkaloids clavepictines A, B and pictamine has been achieved through the highly stereocontrolled quinolizidine ring closure of the conformationally constrained piperidine ring system (2), which bears the chiral centers and appropriate functionality needed for the synthesis of target alkaloids. The absolute stereochemistry of clavepictines and pictamine was verified to be 3R, 4S, 6S, 9aS by the present synthesis.