479633-80-2

Upstream product

• 479633-78-8 3-allyl-6-bromo-2-hydroxy-4-methylbenzaldehyde 
• 139976-21-9 2-bromo-6-hydroxy-4-methylbenzaldehyde 

Downstream Products

• 479633-84-6 (4-bromo-3-dimethoxymethyl-2,5-dimethoxy-6-methylphenyl)acetaldehyde 
• 479633-82-4 1-allyl-4-bromo-3-dimethoxymethyl-2,5-dimethoxy-6-methylbenzene 
• 479634-22-5 2-(4-bromo-3-dimethoxymethyl-2,5-dimethoxy-6-methylphenyl)ethanol 
• 479633-87-9 3-(2-benzyloxyethyl)-6-bromo-2,5-dimethoxy-4-methylbenzaldehyde 
• 479633-89-1 3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-2-vinylbenzaldehyde 
• 479633-86-8 1-(2-benzyloxyethyl)-4-bromo-3-dimethoxymethyl-2,5-dimethoxy-6-methylbenzene 
• 479634-00-9 (S)-6-(2-benzyloxyethyl)-4,7-dimethoxy-2,5-dimethyl-1H-inden-1-ol 
• 479634-07-6 (3aR,8bS)-7-(2-benzyloxyethyl)-5,8-dimethoxy-3a,6-dimethyl-4,8b-dihydro-3aH-indeno[1,2-b]furan 
• 479634-13-4 (S)-5-(2-benzyloxyethyl)-4,7-dimethoxy-2,6-dimethylindan-2-carboxylic acid methyl ester 
• 479633-98-2 (S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylprop-2-en-1-ol 
• 716367-73-6 formic acid (1R,2S)-6-(2-benzyloxyethyl)-2-formyl-4,7-dimethoxy-2,5-dimethylindan-1-yl ester 
• 479634-05-4 (3aR,8bS)-7-(2-benzyloxyethyl)-5,8-dimethoxy-3a,6-dimethyl-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-ol 
• 479634-03-2 (3aR,8bS)-7-(2-benzyloxyethyl)-2-ethoxy-5,8-dimethoxy-3a,6-dimethyl-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan 
• 479634-09-8 (1R,2S)-6-(2-benzyloxyethyl)-1-hydroxy-4,7-dimethoxy-2,5-dimethylindan-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of optically pure (+)-puraquinonic acid and assignment of absolute configuration to natural (-)-puraquinonic acid. Use of radical cyclization for asymmetric generation of a quaternary center

An asymmetric aldol reaction between aldehyde 31 and imide 32, followed at a later stage by ring-closing metathesis (38 → 40), are key reactions used to make optically pure allylic alcohol 40. Radical cyclization of the derived Stork bromo acetals gives lactol ethers 43, which were degraded to generate a quaternary center carrying a methoxycarboxyl group (44 → 47). Compound 47 was converted into (+)-puraquinonic acid; and comparison with a natural sample established that the configuration of the natural compound is 2R (1).

Synthesis of (+)-puraquinonic acid.

(+)-Puraquinonic acid (1a) was synthesized, using a route based on ring-closing metathesis and radical cyclization, the chirality of the quaternary carbon being controlled by a temporary adjacent asymmetric center.