485322-59-6

Upstream product

• 485322-69-8 (E,E,3R,3R)-2,3-oxido-7,11-tetracosadien-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 537665-57-9 (E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido 

Downstream Products

• 485322-62-1 (1R,4R,5R)-1-{(2R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-tetrahydro-pyran-2-yl}-heptadecane-1,4,5-triol 
• 485322-68-7 (S)-3-((E)-(2R,10S)-2-(tert-Butyl-diphenyl-silanyloxy)-10-hydroxy-10-{(2S,6R)-6-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tetrahydro-pyran-2-yl}-dec-5-en-7-ynyl)-5-methyl-5H-furan-2-one 
• 537665-49-9 muconin 4-O-(t-butyldiphenylsilyl)-22-O-(methoxymethyl) diether 
• 537665-81-9 (3S,7R,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanedione 
• 537665-73-9 (2R,3S,7R,8R,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol 
• 537665-75-1 (2R,3S,7R,8R,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate 

Relevant academic research and scientific papers

Total synthesis of muconin

An antitumor acetogenin, muconin, was synthesized through a coupling reaction of a THF-THP segment and a terminal butenolide. The key reactions include 6-exo cyclization of an epoxy tetraol, regioselective cyclization of hydroxy tosylate, and stereoselective reduction of an acyclic ketone adjacent to the 2,6-cis THP ring with Zn(BH4)2.

Stereoselective total synthesis of muconin

An antitumor acetogenin, muconin, was synthesized through a coupling reaction of a THF-THP segment and a terminal butenolide. The key reactions include successive ether-ring formation reaction under acidic and basic conditions or one-pot double cyclization promoted by TBAF and stereoselective reduction of acyclic ketones adjacent to the 2,6-cis THP with Zn(BH4)2.