136031-29-3

Upstream product

• 175520-25-9 (4E)-(+)-3,5-Bis(4-methoxyphenyl)pent-4-ene-1,2-diol acetonide 
• 61171-98-0 (-)-agatharesinol dimethyl ether 
• 51410-44-7 1-(4-methoxylphenyl)-2-propen-1-ol 
• 587885-30-1 (R)-(+)-1-(p-methoxyphenyl)-2-propen-1-ol 
• 289503-61-3 (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 61171-98-0 (+/-)-Di-O-methylagatharesinol 
• 135966-02-8 3-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-1,3-bis-(4-methoxy-phenyl)-propan-1-ol 
• 289503-63-5 (2S,3S)-2-tert-butyldimethylsilyloxy-3,5-bis(4-methoxyphenyl)-5-oxopentanal 
• 289503-60-2 (1S,6R)-6-hydroxy-4'-methoxy-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one 
• 316814-15-0 (2S)-1,2-cyclohexylidenedioxy-3,5-bis(4-methoxyphenyl)pentan-5-ol 
• 587885-31-2 (R)-1,3-bis-(4-methoxyphenyl)pent-4-en-1-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 587885-32-3 (S,S)-acetic acid 2,4-bis(4-methoxyphenyl)-4-oxo-1-triethylsilanyloxymethyl-butyl ester 

Relevant academic research and scientific papers

Regioselective and enantiospecific rhodium-catalyzed allylic alkylation reactions using copper(I) enolates: Synthesis of (-)-sugiresinol dimethyl ether

The transition metal-catalyzed allylic alkylation represents a fundamentally important cross-coupling reaction for the construction of ternary carbon stereogenic centers. We have developed a regioselective and enantiospecific rhodium-catalyzed allylic alk

Synthesis of (-)-sugiresinol dimethyl ether utilizing (-)-quinic acid

(-)-Sugiresinol dimethyl ether, a derivative of (-)-sugiresinol isolated from Cryptomeria japonica, was synthesized through 1,4-conjugate addition of arylmetal reagent to a substituted chiral 2-cyclohcxcn-1-one derived from (- )quinic acid.

Conjugate addition of arylmetal reagents to an α,β-unsaturated ketone. Short syntheses of (-)-agatharesinol dimethyl ether and (-)-sugiresinol dimethyl ether

(-)-Agatharesinol dimethyl ether and (-)-sugiresinol dimethyl ether, derivatives of (-)-agatharesinol and (-)-sugiresinol isolated from Agathis australis and Cryptomeria Japonica, respectively were synthesized starting from a protected D-glyceraldehyde in

Lignans.19. Total synthesis of (-)-O-dimethylsugiresinol, involving asymmetric [4+2] heterocycloaddition of a styrene with a benzylidenepyruvic ester of an α-O-silyl derivative of (D)-erythronolactone

α-O-t-Butyldiphenylsilyl-(D)-erythronolactone [(+)-25] (a new chiral vector) was esterified with 4-methoxybenzylidene pyruvic acid (19). Eu(fod)3 catalyzed [4+2] heterocycloaddition of the latter 1-oxabutadiene with 4- methoxystyrene (as the dienophile), afforded high yields of the endo adduct 23c with 95/5 diastereofacial ratio. Five further steps led to enantiomerically pure natural (-)-O-dimethylsugiresinol (-)-2 in 12% overall yield from the acid 19.

Asymmetric endoselective [4+2] heterocycloadditions of styrene dienophiles with chiral benzylidenepyruvic esters. Total synthesis of (-)-O-dimethylsugiresinol

Eu(fod)3 catalyzed [4+2] heterocycloadditions of para-methoxystyrene 7 with esters 8a-f of benzylidenepyruvic acids (deriving from various chiral alcohols) furnished endo adducts 9a-f with variable diastereoselective ratios (from 58/42 to 86/14). Interestingly, the benzylidenepyruvic esters 8g and 8h, deriving from a new chiral vector, the α-O-silyl ether 6 of (D)-(-)-erythronolactone 5, gave the corresponding endo adducts 9g and 9h with a high diastereoselective ratio (dr ≤95/5). The adduct 9h was used as a precursor in a five-step synthesis of 'natural' (-)-dimethylsugiresinol (1b).

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.

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.