76787-81-0

Upstream product

• 141-97-9 ethyl acetoacetate 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 93-07-2 Veratric acid 

Downstream Products

• 23982-44-7 4-(3',4'-dimethoxyphenyl)-7-methoxycoumarin 
• 23982-43-6 4-(3',4'-dimethoxyphenyl)-7-hydroxycoumarin 
• 4687-40-5 threo-diethyl 2,3-bis-(3,4-dimethoxybenzoyl)butane-1,4-dioate 
• 81581-29-5 erythro-diethyl 2,3-bis-(3,4-dimethoxybenzoyl)butane-1,4-dioate 
• 95622-22-3 diethyl 2,3-bis-(4-hydroxy-3-methoxybenzoyl)butane-1,4-dioate 
• 96931-98-5 diethyl 2,3-bis-(4-benzyloxy-3-methoxybenzoyl)butane-1,4-dioate 
• 4687-40-5 diethyl 2,3-bis-(3,4-dimethoxybenzoyl)butane-1,4-dioate 
• 56606-57-6 ethyl 2-bromo-3-(3,4-dimethoxyphenyl)-3-oxo-propanoate 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 67257-60-7 (+/-)-N-Acetyl-ruspolinon 
• 60890-27-9 1-(3,4-dimethoxyphenyl)-2-(pyrrolidin-2-yl)ethan-1-one 
• 60890-29-1 (3,4-dimethoxybenzoyl)acetic acid 
• 26503-67-3 (+/-)-6,7-di(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydro-indolizine 
• 207272-61-5 2-(Benzo[1,3]dioxole-5-carbonyl)-3-(3,4-dimethoxy-benzoyl)-succinic acid diethyl ester 

Relevant academic research and scientific papers

An Expeditious Synthetic Route to Furolignans having Two Different Aryl Groups

3,4-Dimethyl-2-piperonyl-5-veratrylfuran has been synthesized starting from vanillin and piperonal by employing as the key steps cross-coupling of a bromo β-oxo ester and the sodium salt of another β-oxo ester, affording a 1,4-diketone, and selective reductive removal of an allylic hydroxy group by palladium oxide.

Synthesis and N.m.r. Spectra of 2,6- and 2,4-Diaryl-3,7-dioxabicyclooctanes

A series of isomeric 2,6- and 2,4-diaryl-3,7-dioxabicyclooctanes have been prepared via the corresponding threo, and erythro-dioxo-diesters.Comparison of their 1H and 13C n.m.r. spectra reveals small differences in chemical shifts and coupling constants which could be diagnostic in assigning structures to such compounds.The structure of 4-hydroxysesamin has been confirmed by direct correlation with sesamin.

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.

A New Synthesis of Septicine, a Secophenanthroindolizine Alkaloid

Septicine , an alkaloid isolated from Ficus septica and Tylophora asthmatica, has been synthesized using 2-(3',4'-dimethoxyphenacyl)pyrrolidine (6) and 3,4-dimethoxy-phenylacetyl chloride (11) as the essential intermediates.Condensation of 6 and 11 affords 2-(3',4'-dimethoxyphenacyl)-N-(3'',4''-dimethoxyphenylacetyl)pyrrolidine (12) which on treatment with potassium-t-butoxide furnishes 6,7-di-(3',4'-dimethoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine (13).LAH reduction of 13 affords septicine (1), identical (co-TLC, IR, PMR, m.m.p.) with a natural sample.