91364-70-4

Upstream product

• 77071-95-5 (E)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 38418-31-4 ((E)-piperonylidene)-succinic acid-4-methyl ester 
• 186581-53-3 diazomethane 
• 70381-89-4 methyl hydrogen (E)-2-<3,4-(methylenedioxy)benzylidene>succinate 
• 120-57-0 piperonal 
• 63201-73-0 dimethyl 2-(diethoxyphosphoryl)succinate 
• 106-65-0 Dimethyl succinate 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 75-36-5 acetyl chloride 
• 123591-90-2 (E)-4-[3,4-(methylenedioxy)phenyl]3-ethoxycarbonyl-3-butenoic acid 

Downstream Products

• 150715-15-4 (2E,3E)-3-(methoxycarbonyl)-2-((benzo[d][1,3]-dioxol-6-yl)methylene)-4-(3,4-dimethoxyphenyl)but-3-enoic acid 
• 72622-61-8 α-(trans-3',4'-methylenedioxybenzylidene)-β-(3,4-dimethoxybenzyl)-γ-butyrolactone 

Relevant academic research and scientific papers

Gossypidien, a lignan from stems of Jatropha gossypifollia

A new lignan, gossypidien, has been isolated from the stems of Jatropha gossypifolia. The structure of the compound was deduced from its spectral data, as well as from its synthesis.

First Total Synthesis of (±)-Rhodoconferimide

Starting from vanillin and dimethyl maleate, a concise and efficient racemic total synthesis of the potent antioxidant marine natural product (±)-rhodoconferimide has been carried out via the Wittig reaction, catalytic hydrogenation, selective brominations, and imide formation. An appropriate regioselective double bromination of the aromatic ring was a key step in the synthesis.

Unusual visible-light photolytic cleavage of tertiary amides during the synthesis of cyclolignans related to podophyllotoxin

During the attempted photochemical cyclization of 2,3-bisbenzylidene-γ-hydroxybutyric acid cyclic amide ester, it was observed that a γ-butyrolactone ring was formed, which was concurrent with the release of the amine fragment from the amide. The process occurs with high yield giving rise to the formation of β-apopicropodophyllin and its regioisomer. Additional experiments confirmed the photochemical nature of this transformation, and that it is independent from the photocyclization of the benzylidene groups – a typical reactivity for the members of the fulgide family. In contrast to the latter UV-driven cyclization, the photochemical cleavage of the amide was proven to proceed under irradiation with visible light.

Formal synthesis of (-)-podophyllotoxin through the photocyclization of an axially chiral 3,4-bisbenzylidene succinate amide ester-a flow photochemistry approach

We have developed a strategy for the stereoselective synthesis of cyclolignans related to podophyllotoxin and its derivatives. The crucial step of the synthesis is the photocyclization of a chiral atropoisomeric 1,2-bisbenzylidenesuccinate amide ester, which can be prepared from suitable aromatic aldehydes, diethyl succinate and l-prolinol. The photocyclization was found to be more efficient when irradiation was performed in a home-built continuous flow photochemical reactor. The in-flow irradiation also allowed us to perform the reaction on a multigram scale. The chiral auxiliary was removed by reductive cleavage with the Schwartz's reagent to give the cytotoxic 1R,2R-cis-podophyllic aldehyde, which in turn could be easily reduced to the corresponding alcohol, completing the formal synthesis of (-)-podophyllotoxin.

An Easy Procedure for the Preparation of 3-Methylidenetetrahydrofurans from Dimethyl Succinates

A new synthetic proceduree to obtain 3-methylidenetetrahydrofurans is described, in which the methylidene group is generated during the formation of the tetrahydrofuran ring. These are prepared by reduction of differently substituted dimethyl succinates obtained by Stobbe condensation.

Jatrodien, a lignan from stems of Jatropha gossypifolia

A novel lignan, jatrodien, representing an intermediate in Haworth's biosynthetic scheme for the formation of lignans, has been isolated from the stems of Jatropha gossypifolia. The structure of the compound was derived from its spectroscopic data. Synthesis of the compound, starting from piperonal has been achieved. Copyright

A convenient total synthesis of (+/-)-jatrophan and 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)naphthalene, lignan constituents of Jatropha gossypifolia Linn.

Convenient synthetic routes to (+/-)-jatrophan and 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)naphthalene; the constituents of Jatropha gossypifolia Linn. have been reported.Stobbe condensation of piperonal with dimethyl succinate followed by methylation affords 4-(3',4'-methylenedioxyphenyl)-3-methoxy-carbonyl-methylbut-3-enoate.A second Stobbe condensation with veratraldehyde followed by Bouveault-Blanc reduction affords (+/-)-jatrophan.The aryl naphthalene lignan, 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)naphthalene, has been synthesised from jatrophan by oxidative cyclisation followed by lithium aluminum hydride reduction.

Annelation Reactions of N-Heterocycles to Condensed Pyridones with Bridgehead Nitrogen

The Horner-Wittig reaction of aromatic and heteroaromatic aldehydes with phosphono succinates gives the methylenesuccinates 2a-m and 4a-k in satisfactory yields.The compounds obtained have the E-configuration, as shown by 1H-NMR-spectroscopic and by chemi