869732-30-9

Upstream product

• 869732-29-6 (3S,4R,5S,7R)-8-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-5-methoxy-4-methoxymethoxy-3,7-dimethyl-octane-1,2-diol 
• 869732-13-8 3-(benzyloxy)-5-bromo-2-methoxybenzaldehyde 
• 869732-16-1 (2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-2-methoxy-4-methylpentanal 
• 869732-27-4 (2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol 
• 869732-17-2 (3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol 
• 869732-28-5 1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-enyl)-benzene 
• 869732-23-0 (E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester 
• 869732-15-0 (2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol 
• 869732-26-3 (2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-3-methoxy-5-methyl-hexan-1-ol 
• 869732-14-9 (2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate 
• 869732-24-1 (2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-1-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-3-ol 
• 869732-25-2 [(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-3-methoxy-5-methyl-hexyloxy]-tert-butyl-dimethyl-silane 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 

Downstream Products

• 869732-31-0 1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene 
• 869732-32-1 (2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester 
• 869732-33-2 (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid 
• 869732-09-2 (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide 
• 869732-19-4 (4E,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-3-one 
• 869732-20-7 (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid 20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester 
• 869732-18-3 (2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-hydroxy-11-(methoxymethoxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,8-dienoate 
• 869732-34-3 (4E,10E)-(8S,9S,12S,13R,14S,16R)-20-Benzyloxy-9-hydroxy-8,14,19-trimethoxy-13-methoxymethoxy-4,10,12,16-tetramethyl-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,10,18,20-pentaen-3-one 
• 869732-10-5 1-(benzyloxy)-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-(methoxymethoxy)-2,6-dimethylnon-7-yn-1-yl)benzene 

Relevant academic research and scientific papers

Synthesis of reblastatin, autolytimycin, and non-benzoquinone analogues: Potent inhibitors of heat shock protein 90

A full account of an asymmetric synthesis of reblastatin (1) and the first total synthesis of autolytimycin (2) and related structural compounds is described. The syntheses expand the utility of a highly regio- and diastereoselective hydrometalation aldehyde addition sequence to assemble the fully functionalized ansa chain of the natural products. Also documented is an intramolecular copper-mediated amidation reaction to close the 19-membered macrolactams. The amidation reaction was also employed for the generation of structural derivatives (6-9) of phenolic ansamycins. Ansamycin natural products and selected structural analogues were evaluated in a competitive binding assay to breast cancer cell lysate and a cytotoxicity assay. Both reblastatin (1) and autolytimycin (2) were shown to bind the heat shock protein 90 with enhanced binding activity (～25 nM) than 17-allylamino-17-demethoxygeldanamycin (17-AAG, 4), a geldanamycin (3) derivative currently under evaluation for treatment of cancer (～100 nM).

Total synthesis of reblastatin

Enantioselective total synthesis of reblastatin is described. The synthesis highlights hydrozirconation, transmetalation, aldehyde addition sequence to install E-trisubstituted olefin and C7 stereocenter, and the first use of an intramolecular Buchwald-like amidation reaction to close the 19-membered macrolactam. Copyright