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

• 479634-18-9 (S)-3-[(2R,3S)-3-[3-(2-Benzyloxy-ethyl)-2,5-dimethoxy-4-methyl-6-vinyl-phenyl]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propionyl]-4-isopropyl-oxazolidin-2-one 
• 479633-93-7 (2R,3S)-3-[3-(2-Benzyloxy-ethyl)-2,5-dimethoxy-4-methyl-6-vinyl-phenyl]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propionic acid benzyl ester 
• 479633-91-5 (S)-3-{(2R,3S)-3-[3-(2-Benzyloxy-ethyl)-2,5-dimethoxy-4-methyl-6-vinyl-phenyl]-3-hydroxy-2-methyl-propionyl}-4-isopropyl-oxazolidin-2-one 
• 479633-94-8 (2S,3S)-3-[3-(2-Benzyloxy-ethyl)-2,5-dimethoxy-4-methyl-6-vinyl-phenyl]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propan-1-ol 
• 716367-68-9 (4S)-3-[(2S,3S)-3-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-3-(tert-butyldimethylsilanyloxy)-2-methylpropionyl]-4-isopropyloxazolidin-2-one 
• 716367-69-0 (2S,3S)-3-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-3-(tert-butyldimethylsilanyloxy)-2-methylpropionic acid benzyl ester 
• 716367-67-8 (4S)-3-[(2S,3S)-3-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-3-hydroxy-2-methylpropionyl]-4-isopropyloxazolidin-2-one 
• 716367-70-3 (2R,3S)-3-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-3-(tert-butyldimethylsilanyloxy)-2-methylpropan-1-ol 
• 479634-11-2 (1R,2S)-6-(2-benzyloxyethyl)-1-(imidazole-1-carbothioyloxy)-4,7-dimethoxy-2,5-dimethylindan-2-carboxylic acid methyl ester 
• 479633-96-0 [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane 
• 479634-01-0 (S)-6-(2-benzyloxyethyl)-1-(2-bromo-1-ethoxyethoxy)-4,7-dimethoxy-2,5-dimethyl-1H-indene 
• 479634-09-8 (1R,2S)-6-(2-benzyloxyethyl)-1-hydroxy-4,7-dimethoxy-2,5-dimethylindan-2-carboxylic acid methyl ester 
• 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 
• 479634-05-4 (3aR,8bS)-7-(2-benzyloxyethyl)-5,8-dimethoxy-3a,6-dimethyl-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-ol 

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.