89771-49-3

Upstream product

• 620-08-6 4-methoxypyridine 
• 4801-58-5 N-hydroxypiperidine 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 80324-10-3 1-(3-Benzyloxy-4-methoxy-phenyl)-2-(2S,3aR)-hexahydro-isoxazolo[2,3-a]pyridin-2-yl-ethanol 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 109-06-8 α-picoline 
• 62497-24-9 (3,4-dimethoxyphenyl)propynoic acid methyl ester 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 102652-47-1 Methyl 4-<2-exo,6-exo-6-(3,4-dimethoxyphenyl)-7-oxa-1-azabicyclo<2.2.1>heptan-2-yl>butanoate 
• 102652-52-8 (6R*,8S*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone 
• 24806-77-7 (2S,4R,9aR)-4-(3-Benzyloxy-4-methoxy-phenyl)-octahydro-quinolizin-2-ol 
• 24806-77-7 (2R,4R,9aR)-4-(3-Benzyloxy-4-methoxy-phenyl)-octahydro-quinolizin-2-ol 
• 80324-15-8 Benzoic acid (2R,4R,9aR)-4-(3-benzyloxy-4-methoxy-phenyl)-octahydro-quinolizin-2-yl ester 
• 80324-11-4 1-(3-benzyloxy-4-methoxyphenyl)-3-buten-1-ol 

Downstream Products

• 77092-63-8 2-(p-hydroxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 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 
• 57907-27-4 Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester 
• 77092-60-5 2-(p-benzyloxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 71480-97-2 2-(p-methoxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 68622-78-6 (+)-subcosine I 

Relevant academic research and scientific papers

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

Synthesis of (±)-Lasubine II Using N-Methoxyamines

The synthesis of (±)-lasubine II has been achieved through a three-component allylation capitalizing on the unique properties of N-methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubineII in a single operation. The N-met

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.

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.

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.

Stereoselective Preparation of Acyclic syn-β-Amino Alcohols from β-Hydroxy Ketones via the Corresponding O-Benzyl Oximes

Reduction of β-hydroxy ketone O-benzyl oximes with lithium aluminum hydride in the presence of sodium or potassium methoxide afforded the corresponding syn-β-amino alcohols in highly stereoselective manner.A lythraceae alkaloid, lasubine II, was synthesiz

Stereoselective intramolecular nitrone cycloaddition in the synthesis of Lasubine II.

The intramolecular cycloaddition of α-substituted N-alkenylnitrones 2 leads to the 7-oxa-1-azanorbornanes 6,7, and 8 with a selectivity of ca. 80percent in favor of the exo,exo-disubstituted compound 6.The latter can be reduced to give the all-cis-2,6-disubstituted 4-hydroxypiperidines 4 which are key compounds for the synthesis of certain alkaloids as demonstrated by the synthesis of lasubine II.

A NEW APPROACH TO THE SYNTHESIS OF A LYTHRACEAE ALKALOID, LASUBINE II

A lythraceae alkaloid, (+/-)-lasubine II, is synthesized via an acyclic syn-1,3-amino alcohol which is derived stereoselectively from a β-hydroxy ketone.

Synthesis of (+/-)-Lasubine I and II and (+/-)-Subcosine I

The first total synthesis of lasubine I and II and subcosine I has been achieved.A crucial step of this synthesis involves thermal dipolar cycloaddition of 1-(3,4-dimethoxyphenyl)butadiene with 2,3,4,5-tetrahydropyridine 1-oxide, affording the E and