33187-34-7

Upstream product

• 2156-71-0 N-chloropiperidine 
• 522-33-8 Tripiperidin 
• 22214-39-7 (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one 
• 69730-93-4 (S)-4-[4-Methoxy-3-(2-methoxy-ethoxymethoxy)-phenyl]-octahydro-quinolizin-2-one 
• 851755-92-5 (S)-1-(3-Benzyloxy-4-methoxy-phenyl)-2-(2-methyl-[1,3]dioxolan-2-yl)-ethylamine 
• 110-89-4 piperidine 
• 851755-95-8 5-[(7S,9S)-9-(4-Hydroxy-butyl)-1,4-dioxa-8-aza-spiro[4.5]dec-7-yl]-2-methoxy-phenol 
• 851755-89-0 (S)-1-(3-Benzyloxy-4-methoxy-phenyl)-but-3-enylamine 
• 851755-96-9 C₁₈H₂₅NO₄ 
• 851755-88-9 (R)-2-{N-[(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-but-3-enyl]aminooxy}-1-naphthalen-2-yl-ethanol 
• 851755-94-7 5-[(7S,9R)-9-((E)-4-Benzyloxy-but-1-enyl)-1,4-dioxa-8-aza-spiro[4.5]dec-7-yl]-2-methoxy-phenol 
• 851755-91-4 2-[(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-3-oxo-butyl]-isoindole-1,3-dione 
• 851755-90-3 2-[(S)-1-(3-Benzyloxy-4-methoxy-phenyl)-but-3-enyl]-isoindole-1,3-dione 
• 851755-87-8 3-benzyloxy-4-methoxy-benzaldehyde O-(2-hydroxy-2-naphthalen-2-yl-ethyl)-oxime 

Downstream Products

• 77092-67-2 (4S,9aS)-4-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-octahydro-quinolizin-2-one 
• 77092-66-1 (4S,9aS)-4-(2,6-Dichloro-3-hydroxy-4-methoxy-phenyl)-octahydro-quinolizin-2-one 
• 851755-97-0 (4S,9aS)-4-(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one 
• 851755-98-1 (2S,4S,9aS)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-octahydro-quinolizin-2-ol 

Relevant academic research and scientific papers

Biomimetic Organocatalytic Approach to 4-Arylquinolizidine Alkaloids and Application in the Synthesis of (-)-Lasubine II and (+)-Subcosine II

An enantioselective, biomimetic organocatalytic synthesis of 4-arylquinolizidin-2-ones, key intermediates in the synthesis of several Lythraceae alkaloids, was developed. The methodology features S-proline-mediated Mannich/aza-Michael reactions of readily available arylideneacetones and Δ1-piperideine. The total syntheses of (-)-lasubine II and (+)-subcosine II as well as the formal syntheses of structurally related Lythraceae alkaloids were achieved. The use of Δ1-pyrroline in the Mannich/aza-Michael reaction provides enantiomerically enriched 5-arylindolizidin-7-ones, which are precursors to nonopiate antinociceptive agents.

Asymmetric synthesis of (+)-abresoline

The first asymmetric synthesis of (+)-abresoline has been achieved starting from the (S)-1-(aryl)homoallylic amine, which was prepared enantioselectively by the method based on allylation of the (R)-2′-(2-naphthyl)-bearing hydroxyoxime ether. This synthetic route employs the TiCl4-induced intramolecular Mannich-type cyclization of the 1-azadiene-bearing ketal amine as the key steps to afford stereoselectively the cis-2,6-disubstituted piperidine, followed by CBr4/PPh3-induced dehydrocyclization for the elaboration of the amino alcohol to the trans-4-arylquinolizidine.

Synthetic studies on the lythraceae alkaloids-IX1 1 Other papers in this series: I.J. Quick and R. Oterson, Tetrahedron Letters 745 (1977); II, Ref. 8a; III, Ref. 8b; IV, Ref. 3a; V, Ref. 14; VI, Ref. 12; VII, Ref. 18; VIII, Ref. 13. Vanadium (V) oxidation of some seco-alkaloids

Seco-alkaloids 4-7 were treated with VOF3 and VOCl3, under a variety of conditions. No coupled products were detected. However, ring chlorinated and side-chain oxidized products were obtained from the VOCl3 oxidation of 4 and 7 respectively. The generality of the ring chlorination reaction was confirmed by chlorination of simple 0-methoxy phenols under these conditions to yield 17 and 23. In certain cases, 21 and 22, intermolecular coupling occurs in preference to chlorination.