251556-95-3

Upstream product

• 100-53-8 phenylmethanethiol 
• 251556-94-2 (S)-4-Benzyl-3-[(3S,4S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enoyl]-oxazolidin-2-one 
• 251556-93-1 (S)-4-Benzyl-3-[(2S,3R,4R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-2-methylsulfanyl-hept-6-enoyl]-oxazolidin-2-one 
• 251556-92-0 (S)-4-Benzyl-3-[(2S,3R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-2-methylsulfanyl-hept-6-enoyl]-oxazolidin-2-one 
• 470467-69-7 (2R,3R)-3-hydroxy-2,4-dimethylpent-4-enoic acid N-methoxy-N-methylamide 
• 171013-53-9 (4R,5S)-3-((2R,3R)-3-Hydroxy-2,4-dimethyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 180628-70-0 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide 
• 171013-57-3 (2R,3R)-3-(tert-butyldimethylsilyloxy)-2,4-dimethylpent-4-enal 
• 69739-34-0 t-butyldimethylsiyl triflate 

Relevant academic research and scientific papers

Stereocontrolled preparation of the C1-C14 polyene fragment of benzenic ansamycin antibiotics ansatrienin A and B

A practical synthesis of the C1-C14 polyene unit 5 in ansatrienin A (mycotrien l), 1a, and other ansamycin antibiotics is described which involves elaboration of the chiral unsaturated aldehyde 6 and phosphonate 7, followed by coupling of the building blocks by Horner-Emmons-olefination and Duthaler's aldolation. The synthesis of 6 successfully applies two consecutive Evans-aldol reactions for constructing the carbon backbone.