144409-60-9

Upstream product

• 184535-17-9 (-)-(2S)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 184535-06-6 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 2508-29-4 5-hydroxypentylamine 
• 15001-27-1 O-methyldehydrozingerone 
• 119910-09-7 N-tert-butoxycarbonyl-2-ethoxypiperidine 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 110-89-4 piperidine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 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 
• 2156-71-0 N-chloropiperidine 
• 1202039-12-0 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester 

Downstream Products

• 68622-78-6 (+)-subcosine I 
• 68622-77-5 (-)-Lasubine I 
• 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

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.

Strategies for the Asymmetric Construction of Pelletierine and its Use in the Synthesis of Sedridine, Myrtine, and Lasubine

Three methods for the asymmetric synthesis of both enantiomers of pelletierine 6 are reported. Bella's proline-based Mannich process gave (R)- and (S)-Cbz-protected 6 in good yields from Δ1-piperideine 14 and in reasonable enantiomeric excess (74–80 % ee). An intramolecular aza-Michael, cinchona-based, organocatalytic method is also reported. With commercially available 9-amino quinine (24a) and quinidine (24b) catalysts, Cbz-protected α,β-unsaturated ketone 23 also gave (R)- and (S)-Cbz-protected 6 in good yields and enantiomeric excess (90–99 % ee). This material was used to synthesize both optically active forms of deoxyhalofuginone (26), an analogue of febrifugine which is of interest as an anti-fibrotic agent. Finally, a resolution of racemic pelletierine using (R)- and (S)-mandelic acid 27 is reported. This scalable method gave both enantiomers of Cbz- and Boc-protected 6 in excellent enantiomeric excess (≥ 99 %). Both highly enantioenriched forms of 6 (obtained from the resolution study) were used to synthesize several alkaloids. Firstly, (–)-(S)-Cbz-protected pelletierine 17 was used to prepare naturally occurring sedridine (32) and its epimer allosedridine (8). Then the preparation of both enantiomers of the quinolizidine myrtine (33) by an olefination-intramolecular aza-Michael sequence is reported. Finally, the synthesis of the epimeric quinolizidine alkaloids, lasubine I (34) and lasubine II (35), from (+)- and (–)-Boc-protected pelletierine (29) respectively, is discussed.

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.

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

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

Asymmetric synthesis of quinolizidine alkaloids (-)-lasubine I, (-)- lasubine II and (+)-subcosine II

The enantioselective synthesis of (-)-lasubine I 1 and the first asymmetric synthesis of (-)-lasubine II 2 and (+)-subcosine II 3 is described. The key step is the intramolecular cyclization of N-acyliminium ion 4 which is derived from (S)-aminoester 6.

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.

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.