172922-64-4

Upstream product

• 172922-62-2 (Z)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 172922-63-3 2,3-bis(3,4-dimethoxyphenyl)-2-hydroxypropanoic acid 
• 186581-53-3 diazomethane 

Downstream Products

• 173093-54-4 (Z)-2,3-Bis-(3,4-dimethoxy-phenyl)-prop-2-en-1-ol 

Relevant academic research and scientific papers

Oxidative intramolecular coupling of 2,3-disubstituted phenyl acrylic acids and derivatives promoted by di-tert-butylperoxide

Polymethoxy-substituted phenanthrene-9-carboxylic acids or their methylate are key intermediates for the synthesis of tylophora alkaloids and their analogs. An intramolecular oxidative coupling reaction of unfunctionalized 2,3-disubstituted phenyl acrylic

Iron(III) chloride catalyzed oxidative coupling reaction of 1,2-diarylethylene derivatives

A nontoxic FeCl3 catalyzed intramolecular oxidative coupling reaction was developed for mild synthesis of a series of phenanthrenes with different substituents. The method involves cross dehydrogenative coupling of a variety of 1,2-diarylethyle

A simple and efficient oxidative coupling of aromatic nuclei mediated by manganese dioxide

Oxidative intramolecular coupling of the aryl rings of various stilbenes for direct construction of the phenanthrene ring system is promoted efficiently by manganese dioxide-trifluoroacetic acid at room temperature in excellent yields. This approach is also applied to the intermolecular biaryl coupling of 2-naphthols, 2-naphthalenethiol, 2-naphthylamine, a phenol ether and a phenol under very mild conditions. An electron-transfer mechanism is proposed in which manganese dioxide acts as a two-electron oxidant.

Synthesis of phenanthro[9,10-b]indolizidin-9-ones, phenanthro[9,10-b] quinolizidin-9-one, and related benzolactams by Pd(OAc)2-catalyzed direct aromatic carbonylation

Phenanthro[9,10-b]indolizidin-9-ones, phenanthro[9,10-b]-quinolizidin-9- one, and related benzolactams were synthesized by benzolactam ring formation using Pd(OAc)2-catalyzed direct aromatic carbonylation. This also constitutes a formal synthesis of the representative phenanthroindolizidine and -quinolizidine alkaloids (±)-tylophorine, (±)-antofine, and (±)-cryptopleurine. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

(Z)-2,3-Bis(3,4-dimethoxyphenyl)propenoic Acid

The crystal structure determination demonstrates unambiguously that the title compound, C19H20O6, has the Z configuration.The compound was synthesized starting from 2,3-bis(3,4-dimethoxyphenyl)-2-hydroxypropanoic acid, which was in turn obtained by an alkaline treatment of trans-1,3-bis(3,4-dimethoxyphenyl)-2,3-epoxy-1-propanone. 1H NMR data for the title compound and its methyl ester are reported.

Phenanthroindolizidine and Related Alkaloids: Synthesis of Tylophorine, Septicine, and Deoxytylophorinine

Tylophorine (1) is synthesized in two ways.The first method begins with the synthesis of the amide-ester (7), which on reaction, successively, with triethyloxonium fluoroborate and sodium borohydride, gives the aminoester (8) selectively; hydrolysis and polyphosphoric acid-catalysed ring-closure of compound (9) gives the ketone (10) which yields tylophorine (1) on Clemmensen reduction.An alternative approach is by a biogenetically patterned sequence which involves condensation of (3,4-dimethoxybenzoyl)acetic acid (26) with 1-pyrroline (24) generated either in situ from putrescine by pea-seedling diamine oxidase or from ornithine by oxidation with N-bromosuccinimide; the product (16) condenses with 3,4-dimethoxyphenylacetaldehyde in benzene to give an enamine .This undergoes cyclisation and dehydration in methanol; sodium borohydride reduction then gives the alkaloid septicine (19) which, on oxidation with thallium(III) trifluoroacetate, yields tylophorine (1).Deoxytylophorinine (34) is made in an exactly analogous manner to the latter method for tylophorine.