220300-07-2

Upstream product

• 5533-00-6 3-methoxy-4-methoxymethoxy-benzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 2309-07-1 Methyl ferulate 
• 107-30-2 chloromethyl methyl ether 
• 121-33-5 vanillin 

Downstream Products

• 2309-07-1 Methyl ferulate 
• 169959-08-4 3-Methoxy-4-methoxymethoxy cinnamic acid 
• 220300-09-4 (E)-3-{4-[(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-octa-2,7-dienyloxy]-3-methoxy-phenyl}-acrylic acid methyl ester 
• 220300-13-0 (E)-3-{4-[(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-octa-2,7-dienyloxy]-3-methoxy-phenyl}-prop-2-en-1-ol 

Relevant academic research and scientific papers

First total synthesis of Boehmenan

The first total synthesis of dilignan Boehmenan has been achieved. A biomimetic oxidative coupling of the ferulic acid methyl ester in the presence of silver oxide is the crucial step in the synthesis sequence, generating the dihydrobenzofuran skeleton. Hydroxyl group was protected with DHP and reducted with LiAlH 4 to afford the intermediate diol. The diol was condensated with the derivative of ferulic acid, then removed the protecting groups, to get Boehmenan. Meanwhile, a study on the ring-opening reaction of the intermediate dihydrobenzofuran neolignan under base conditions was described.

Total synthesis of (±)-divanillyltetrahydrofuran ferulate

A convenient method for the synthesis of sesquilignan threo- and erythro-(±)-divanillyltetrahydrofuran ferulate is described. The synthesis was based on a unified synthetic strategy involving two Stobbe condensations to give the skeleton of lignan, and then reduction reaction to form meso- and threo-(±)-secoisolanciresinol. meso- and threo-(±)-secoisolanciresinol were separated by flash column chromatography, followed by intramolecular reaction with TsCl to afford the key intermediate meso- or threo-(±)-shonanin, then condensation with ferulaic acid to obtain sesquilignan threo- or its analogue erythro-(±)- divanillyltetrahydrofuran ferulate. Indian Academy of Sciences.

Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: First total synthesis of (-)-4-O-(6'-hydroxy- 7'(9')-dehydro- 6',7'-dihydrogeranyl)coniferol

An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O- (6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol.