132621-84-2

Basic information

• Product Name: (3R,4S,6S,9aS)-6-[Deca-1(E),3(E)-dienyl]-4-methylperhydroquinolizin-3-ol
• Synonyms: Clavepictine B
• CAS NO: 132621-84-2
• Molecular Formula: C₂₀H₃₅NO
• Molecular Weight: 305.50805
• Mol File: 132621-84-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3R,4S,6S,9aS)-6-[Deca-1(E),3(E)-dienyl]-4-methylperhydroquinolizin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,6S,9aS)-6-[Deca-1(E),3(E)-dienyl]-4-methylperhydroquinolizin-3-ol(132621-84-2)
• EPA Substance Registry System: (3R,4S,6S,9aS)-6-[Deca-1(E),3(E)-dienyl]-4-methylperhydroquinolizin-3-ol(132621-84-2)

Safety Data

• Hazardous Substances Data: 132621-84-2(Hazardous Substances Data)

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 articles and documents

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.

Enantioselective total synthesis of the marine alkaloid clavepictines A and B

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