184221-13-4

Upstream product

• 212079-06-6 2-(pent-4-yn-1-yloxy)isoindoline-1,3-dione 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 5390-04-5 pent-1-yn-5-ol 
• 184220-93-7 (E)-1-(3,4-Dimethoxy-phenyl)-4,4-dimethoxy-pent-1-en-3-one 
• 184220-92-6 (E)-5-(3,4-Dimethoxy-phenyl)-pent-4-ene-2,3-dione 
• 123-11-5 4-methoxy-benzaldehyde 
• 64304-83-2 trans-1-(4-methoxyphenyl)-2-methoxyethene 
• 184221-11-2 3-[4-(3,4-dimethoxyphenyl)-5-(4-methoxyphenyl)pyridin-2-yl]propan-1-ol 
• 816462-34-7 3,4-dimethoxyphenylpropioloyl chloride 
• 22511-06-4 3,4-dimethoxyphenylpropiolic acid 
• 4136-21-4 p-methoxybenzoylmethanol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 637-69-4 4-Methoxystyrene 

Relevant academic research and scientific papers

A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine

A concise and flexible procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope and good functional group tolerance. The total synthesis of (±)-seco-antofine and (±)-septicine were realized employing this strategy.

Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl-substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium-catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results help to further advance functionalized cyclic carbonates as useful and reactive intermediates in natural product synthesis.

A General Cp*CoIII-Catalyzed Intramolecular C?H Activation Approach for the Efficient Total Syntheses of Aromathecin, Protoberberine, and Tylophora Alkaloids

Herein, we report a Cp*CoIII-catalyzed C?H activation approach as the key step to create highly valuable isoquinolones and pyridones as building blocks that can readily be applied in the total syntheses of a variety of aromathecin, protoberberine, and tylophora alkaloids. This particular C?H activation/annulation reaction was achieved with several terminal as well as internal alkyne coupling partners delivering a broad scope with excellent functional group tolerance. The synthetic applicability of this protocol reported herein was demonstrated in the total syntheses of two Topo-I-Inhibitors and two 8-oxyprotoberberine cores that can be further elaborated into the tetrahydroprotoberberine and the protoberberine alkaloid core. Moreover these building blocks were also transformed to six different tylophora alkaloids in expedient fashion.

PHENANTHROINDOLIZIDINE AND PHENANTHROQUINOLIZIDINE ALKALOID HAVING A HYDROXYL GROUP ON THE PHENANTHRENE RING THEREOF, PREPARATION METHOD AND USE THEREOF

A phenanthroindolizidine and phenanthroquinolizidine alkaloid having a hydroxyl group on the phenanthrene ring thereof was synthesized, which exhibits potent activity as an anticancer agent against, such as breast cancer, lung cancer, and prostate cancer.

Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines

Phenanthroindolizidines and phenanthroquinolizidines were concisely synthesized by the reductive decyanization of cyano-promoted intramolecular aza-Diels-Alder cycloadducts followed by aryl-aryl coupling. Cyano groups were removed from α-aminoacrylonitriles via treatment with sodium borohydride in 2-propanol in almost quantitative yields; a possible mechanism was proposed and examined using D-labeling experiments. A systematic study of the effects of the phenanthrene substitution pattern on the anticancer activity against three human cancer cell lines was discussed. (Chemical Equation Presented).

Rhodium(III)-catalyzed intramolecular annulation through C-H activation: Total synthesis of (±)-antofine, (±)-septicine, (±)-tylophorine, and rosettacin

Annulation: The efficient synthesis of 3-hydroxyalkyl isoquinolones and 6-hydroxyalkyl 2-pyridones is enabled through the intramolecular annulation of alkyne-tethered hydroxamic esters (see scheme, Cp= pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional-group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant.

Total synthesis of the tylophora alkaloids rusplinone, 13aα- secoantofine, and antofine using a multicatalytic oxidative aminochlorocarbonylation/Friedel-Crafts reaction

A rapid synthetic approach to the tylophora alkaloids antofine and 13aα-secoantofine is presented that makes use of a multicatalytic oxidative aminochlorocarbonylation/Friedel-Crafts reaction as the key step. This reaction, along with a one-pot, three-ste

A unified strategy for the synthesis of phenanthroizidine alkaloids: Preparation of sterically congested pyridines

Total syntheses of the representative phenanthroizidine alkaloids, tylophorine and antofine, and of their seco congeners, septicine and julandine, have been completed from sterically congested 3,4-diarylpyridines prepared by a modified Knoevenagel-Stobbe