42922-10-1

Upstream product

• 118199-01-2 2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene 
• 79238-81-6 4-[(3,4-dimethoxyphenyl)ethynyl]-1,2-dimethoxybenzene 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 65462-22-8 4-benzyloxycarbonylamino-6-diazo-5-oxo-hexanoic acid methyl ester 
• 2859-78-1 4-Bromoveratrole 
• 196494-92-5 Trifluoro-methanesulfonic acid (R)-6-bromo-1,2,3,5,8,8a-hexahydro-indolizin-7-yl ester 
• 126378-42-5 4-methoxy-3-(trisopropylsilyl)pyridine 
• 196494-87-8 (R)-2-But-3-enyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 196494-88-9 (R)-2-(3-Chloro-propyl)-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 135365-68-3 (R)-6-Triisopropylsilanyl-2,3,8,8a-tetrahydro-1H-indolizin-7-one 
• 88790-37-8 (2S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-2-carboxylate 
• 101130-03-4 tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 

Downstream Products

• 482-20-2 (R)-tylophorine 

Relevant academic research and scientific papers

Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization

A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azet

Iminium ion-enamine cascade cyclizations: Facile access to structurally diverse azacyclic compounds and natural products

A one-pot, mild, two-component iminium ion-enamine cascade reaction to construct structurally diverse azacyclic frameworks from l-proline and l-pipecolic acid, and its application to indolizidine and quinolizidine alkaloids and azasteroids, is reported.

Synthesis of (+)-septicine using intramolecular McMurry coupling: A Chiron approach

Total synthesis of secophenanthroindolizidine alkaloid (+)-septicine 1 was accomplished using the McMurry coupling for the construction of indolizidine ring, using L-glutamicacid as chiral source. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Synthesis of (-)-Septicine and (-)-Tylophorine

A concise asymmetric synthesis of (-)-septicine (1) and (-)-tylophorine (2) was accomplished with a high degree of stereocontrol in eight and nine steps, respectively. Addition of 4-(1-butenyl)magnesium bromide to 1-acylpyridinium salt 3, prepared in situ from 4-methoxy-3-(triisopropylsilyl)pyridine and the chloroformate of (-)-trans-2-(α-cumyl)cyclohexanol, gave a 91% yield of diastereomerically pure dihydropyridone 7. Oxidative cleavage of 7 and subsequent reduction provided alcohol 6 in 81% yield. Conversion of 6 to the chloride followed by treatment with sodium methoxide gave indolizidinone 9 in high yield. Bromination and conjugate reduction of 9 with L-Selectride, and trapping the intermediate enolate with N-(5-chloro-2-pyridyl)triflimide, provided bromovinyl triflate 11. Palladium-catalyzed cross-coupling of excess (3,4-dimethoxyphenyl)zinc bromide and 11 gave (-)-septicine (1). On the basis of this synthesis, (-)-1 was assigned the R configuration. Reaction of 1 with vanadium(V) trifluoride oxide in TFA/CH2Cl2 effected oxidative coupling to give a 68% yield of (-)-tylophorine (2).