625450-84-2

Upstream product

• 625450-94-4 (3S,4R,5S,7R)-4-(tert-butyldimethylsilanoxy)-3,7-dimethyl-5-methoxy-8-(5-nitro-2,3,6-trimethoxyphenyl)octene 
• 326606-16-0 (3S,5S,6S)-3-[(1S,3R)-1-hydroxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one 
• 326606-26-2 (3S,5S,6S)-3-[(1S,3R)-1-methoxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one 
• 474411-07-9 (2R,3S,5R)-2-hydroxy-3-methoxy-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexanoic acid methyl ester 
• 474411-10-4 (3R,4S,6R)-2,6-dimethyl-3-hydroxy-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene 
• 474411-08-0 (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexanal 
• 474411-09-1 (3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptan-2-one 
• 474410-95-2 (3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptan-2-ol 
• 474410-94-1 (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexanoic acid methyl ester 
• 474410-96-3 (3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene 
• 474410-93-0 (2R,3S,5R)-2-[(1S,2S)-2-hydroxy-1,2-bis-(4-methoxy-phenyl)-ethoxy]-3-methoxy-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexanoic acid methyl ester 
• 474410-97-4 (2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol 
• 474411-12-6 (2R,3R,4S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-2,6-dimethyl-7-(2,3,6-trimethoxy-5-nitro-phenyl)-heptanal 
• 474411-20-6 (2S,3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptan-1-ol 

Downstream Products

• 625450-86-4 (6S)-6-methoxy-2,8-dimethyl-(7S)-7-(triethylsilanoxy)-nona-2,4,8-trienoic acid {3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R,6S)-2,6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenyl}amide 

Relevant academic research and scientific papers

Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin: Asymmetric glycolate aldol reactions and biological evaluation

The total synthesis of (+)-geldanamycin (GA), following a linear route, has been completed using a demethylative quinone-forming reaction as the last step. Key steps include the use of two new asymmetric boron glycolate aldol reactions. To set the anti-C11,12 hydroxymethoxy functionality, (S,S)-5,6-bis-4-methoxyphenyldioxanone 8 was used. Methylglycolate derived from norephedrine 5 set the C6,7 methoxyurethane stereochemistry. The quinone formation step using nitric acid gave the non-natural o-quino-GA product 55 10: 1 over geldanamycin. Other known oxidants gave an unusual azaquinone product 49. o-Quino-GA 55 binds Hsp90 with good affinity but is less cytotoxic compared to GA.