112840-40-1

Upstream product

• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 112840-38-7 2-(3,4-dimethoxyphenyl)methylenecyclopropane 
• 15001-27-1 O-methyldehydrozingerone 
• 119910-09-7 N-tert-butoxycarbonyl-2-ethoxypiperidine 
• 620-08-6 4-methoxypyridine 
• 2859-78-1 4-Bromoveratrole 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 60234-90-4 4-(3,4-dimethoxy-phenyl)-but-3-en-2-one 
• 110-89-4 piperidine 
• 112840-47-8 1-chloro-1-methyl-2-(3,4-dimethoxyphenyl)cyclopropane 
• 6380-23-0 3,4-dimethoxystyrene 
• 206749-06-6 1-[1-(3,4-Dimethoxy-phenyl)-3-trimethylsilanylmethyl-but-3-enyl]-6-hydroxy-piperidin-2-one 
• 206749-04-4 1-[1-(3,4-Dimethoxy-phenyl)-3-trimethylsilanylmethyl-but-3-enyl]-piperidine-2,6-dione 
• 748157-67-7 1-(3,4-dimethoxyphenyl)-3-(trimethylsilyloxy)buta-1,3-diene 

Downstream Products

• 88931-06-0 (+/-)-subcosine I 
• 88931-04-8 (2RS,4RS,9aSR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-ol 
• 89771-50-6 (+/-)-2-episubcosine II 
• 89771-49-3 (±)-lasubine II 
• 88931-05-9 4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizin-2-ol 

Relevant academic research and scientific papers

One-pot preparation of quinolizidin-2-one and indolizidin-7-one ring systems. Concise total synthesis of (±)-myrtine, (±)-lasubine II, and (-)-indolizidine 223AB

A highly efficient approach to the quinolizidine alkaloids (±)-myrtine (4) and (±)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/

Tandem N-acyliminium-Michael addition reaction. An efficient total synthesis of the quinolizidine alkaloids (+/-)-myrtine and (+/-)-lasubine II

A short and efficient preparation of the quinolizidine alkaloids (±)-lasubine II (1) and (±)-myrtine (2) is described featuring the tandem N-acyliminium ion-Michael addition of 2-trimethylsilyloxy butadienes to ethoxycarbamate 4 promoted by TMSOTf.

α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines

Enolizable cyclic imines, obtained in situ from their corresponding lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF3 etherate. β-Aminoesters derived from ester enolates can be converted to the corresponding β-lactams.

Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II

A series of high-yielding silver(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cycliz

A method for synthesizing compound of [...]

The invention relates to quinolizidine compounds, particularly a synthesis method of a quinolizidine ketone compound. The method comprises the following steps: carrying out aza Diels-Alder reaction on a compound 1 chloroacylbutyl amine in a halohydrocarbon solvent or alcohol solvent at 0-30 DEG C under the actions of fluoroform sulfonic anhydride, silane, organic base and diolefin, carrying out hydrochloric acid treatment, extracting, drying, concentrating, and purifying to obtain a compound 2 chloro-2,3-dihydro-4-pyridone; carrying out iodo reaction on the compound 2 chloro-2,3-dihydro-4-pyridone in a ketone solvent at 30-90 DEG C under the action of an iodate, extracting, drying, concentrating and purifying to obtain a compound 3-iodo-2,3-dihydro-4-pyridone; and reacting the compound 3 in a halohydrocarbon solvent at 60-100 DEG C under the actions of an initiator and a reducer, concentrating, and purifying to obtain the compound 4 quinolizidine ketone compound.

Synthetic applications of sulfur-substituted indolizidines and quinolizidines

Starting from the sulfur-substituted indolizidines and quinolizidines, a few useful synthetic transformations have been developed and the synthesis of some natural products including indolizidine 209D, epimyrtine, lasubine II, 8a-epi-dendroprimine, and 5-

Rhodium-catalyzed intramolecular conjugate addition of vinylstannanes to?dihydro-4-pyridones: a simple method for stereoselective construction of 1-azabicyclic alkaloids

A straightforward route for the stereoselective synthesis of unsaturated quinolizidines and related higher homologs has been developed. Our results revealed that the rhodium complex [RhCl(cod)]2 is an effective catalyst for the intramolecular c

A synthesis of the quinolizidine alkaloids (±)-lasubine I and (±)-lasubine II

A total synthesis of (±)-lasubine I and (±)-lasubine II has been achieved in six steps from a β-hydroxyallylsilane synthon using intramolecular cyclization of allylsilane on N-acyliminium ion as a key step.

A highly stereocontrolled, four-step synthesis of (±)-lasubine II

A four-step synthesis of (±)-lasubine II (1) from 4-methoxypyridine is described. The addition of benzyl chloroformate to a mixture of (3,4-dimethoxyphenyl)magnesium bromide and 4-methoxypyridine gives the N-acetyl-2,3-dihydro-4-pyridone 3 on workup with aqueous acid. Copper-mediated conjugate addition of (4-chlorobutyl)magnesium bromide to 3 affords cis-2,6-disubstituted piperidine 6. Catalytic hydrogenolysis of 6 with palladium on carbon in the presence of lithium carbonate gives an 82% yield of quinolizidinone 7. Reduction of 7 with lithium trisiamylborohydride provides (±)-lasubine II (1). The four-step total synthesis is carried out in 28% overall yield with excellent stereocontrol.