135965-97-8

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 51410-44-7 1-(4-methoxylphenyl)-2-propen-1-ol 
• 75-07-0 acetaldehyde 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 

Downstream Products

• 136031-29-3 (-)-sugiresinol dimethyl ether 
• 61171-98-0 (-)-agatharesinol dimethyl ether 
• 4825-70-1 (+)-Di-O-methylhinokiresinol 
• 175520-25-9 (4E)-(+)-3,5-Bis(4-methoxyphenyl)pent-4-ene-1,2-diol acetonide 
• 135966-01-7 (2S,3S)-3,5-Bis(4-methoxyphenyl)pentane-1,2,5-triol 

Relevant academic research and scientific papers

First asymmetric synthesis of (-)-sugiresinol dimethyl ether

Efficient enantioselective synthesis of (-)-sugiresinol dimethyl ether was accomplished based upon two asymmetric processes: asymmetric β-alkylation of α,β-unsaturated aldimines and enantioselective dihydroxylation of olefins.

Enantioselective Iridium-Catalyzed α-Allylation with Aqueous Solutions of Acetaldehyde

The enantioselective α-allylation of aqueous solutions of acetaldehyde using iridium- A nd amine-catalyzed substitution of racemic allylic alcohols is described. The method utilizes a readily available, safely handled aqueous solution of acetaldehyde and furnishes ?,?-unsaturated aldehydes in good yields and greater than 99% enantiomeric excess. The synthetic potential of the method is demonstrated with the enantioselective formal syntheses of heliannuols C and E as well as heliespirones A and C.

Enantioselective total synthesis of the di-O-methyl ethers of (-)-agatharesinol, (+)-hinokiresinol and (-)-sugiresinol, characteristic norlignans of Coniferae

Facile enantioselective syntheses of the di-O-methyl ethers of the norlignans, (-)-agatharesinol (-)-1a, (+)-hinokiresinol (+)-2a and (-)-sugiresinol (-)-3a are described. Grignard addition of vinylmagnesium bromide to an aldimine (-)-13, prepared from the tert-butyl ester 11 and 4-methoxycinnamaldehyde 12, afforded a homochiral vinyl aldehyde, (-)-3-(4-methoxyphenyl)pent-4-enal (-)-14 in > 95% ee, which was converted into a diastereoisomeric mixture of 1,3-bis(4-methoxyphenyl)pent-4-en-1-ols (3R)-6 by a second Grignard reaction with 4-methoxyphenylmagnesium bromide. Sharpless' asymmetric dihydroxylation of the vinyl alcohols (3R)-6 proceeded diastereoselectively to give the triol of desired relative stereochemistry (2S,3S)-7. This, upon dehydration, afforded (-)-di-O-methylsugiresinol (-)-3b, the subsequent acid-catalysed cyclization of which gave (-)-di-O-methyl agatharesinol (-)-1b. (+)-Di-O-methylhinokiresinol (+)-2b was readily obtained by the dehydration of the vinyl alcohols (3R)-6.