68681-73-2

Basic information

• Product Name: 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-
• Synonyms: 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, [2S-(2a,4b,9aa)]-;(-)-Lasubin II; (-)-Lasubine II; Lasubine II
• CAS NO: 68681-73-2
• Molecular Formula: C17H25 N O3
• Molecular Weight: 291.39
• Mol File: 68681-73-2.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-(68681-73-2)
• EPA Substance Registry System: 2H-Quinolizin-2-ol,4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-(68681-73-2)

Safety Data

• Hazardous Substances Data: 68681-73-2(Hazardous Substances Data)

Upstream product

• 263247-25-2 (2S,4S,6S)-(-)-2-(3,4-dimethoxyphenyl)-6-(4-hydroxybutyl)-piperidin-4-ol 
• 144409-60-9 (4S,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 69622-67-9 benzyl 2-hydroxypiperidine-1-carboxylate 
• 87905-98-4 5-<(benzyloxycarbonyl)amino>pentanol 
• 2858-66-4 (-)-pelletierine 
• 2858-67-5 1-[(2S)-piperidin-2-yl]acetone 
• 1402830-66-3 (+)-(E)-tert-butyl 2-(4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate 
• 1214914-34-7 (S)-2-(2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1202039-12-0 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester 
• 2508-29-4 5-hydroxypentylamine 
• 184535-06-6 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 184535-17-9 (-)-(2S)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 522-33-8 Tripiperidin 

Downstream Products

• 77092-63-8 2-(p-hydroxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 71480-97-2 2-(p-methoxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 77092-60-5 2-(p-benzyloxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 10183-64-9 Decinin 
• 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 
• 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 
• 68622-78-6 (+)-subcosine I 

Relevant articles and documents

Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones

Enantiopure β-amino ketone derivatives were synthesized by decarboxylative Mannich reaction of chiral N-tert-butanesulfinyl imines with β-keto acids and were subsequently transformed into cis-2,6-disubstituted piperidin-4-ones through an organocatalyzed condensation with aldehydes. Both enantiomers were accessible from the same precursors by inverting the order in the reaction sequence of the aldehydes involved in the imine formation and the intramolecular Mannich condensation. The synthesis of the piperidine alkaloids (+)-241D, (-)-epimyrtine, and (-)-lasubine II demonstrated the utility of this methodology.

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.

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.