71480-97-2

Upstream product

• 68622-77-5 (2S,9aS)-4-(3,4-Dimethoxy-phenyl)-octahydro-quinolizin-2-ol 
• 15823-04-8 methyl 3-(4-methoxyphenyl)propionate 
• 110-89-4 piperidine 
• 1384454-07-2 C₁₄H₂₀NO₂⁽¹⁺⁾*ClO₄^(1-) 
• 1384454-08-3 C₁₇H₂₃NO₂ 
• 7400-08-0 para-coumaric acid 
• 3943-97-3 methyl p-hydroxycinnamate 
• 6272-45-3 4-benzyloxycinnamic acid 
• 84184-51-0 Z-methyl 3-(4-benzyloxy)phenylacrylate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 77092-63-8 2-(p-hydroxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 74-88-4 methyl iodide 
• 221664-11-5 (4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one 
• 68681-73-2 (-)-(2S,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine 

Downstream Products

• 71480-98-3 (Z)-2-Chloro-3-(4-methoxy-phenyl)-acrylic acid (2S,4S,9aS)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester 
• 71480-99-4 2,2,3-Trichloro-3-(4-methoxy-phenyl)-propionic acid (2S,4S,9aS)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester 

Relevant academic research and scientific papers

Total synthesis of (±)-decinine via an oxidative biaryl coupling with defined axial chirality

The total synthesis of (±)-decinine has been achieved. The key steps in the synthesis involved the formation of lasubine II via a gold catalyzed annulation of 1-(but-3-yn-1-yl)piperidine and the formation of the 12-membered ring of decinine (1) with complementary atropselectivity via a VOF 3-mediated oxidative biaryl coupling reaction.

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.