170897-53-7

Upstream product

• 29161-71-5 β-1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-D-ribofuranose 
• 38821-11-3 2-(triphenylphosphoranylidene)acetamide 
• 478367-12-3 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate 
• 96690-02-7 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 
• 170590-38-2 3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-furan-2,5-dione 

Downstream Products

• 16755-07-0 showdomycin 

Relevant academic research and scientific papers

Syntheses of showdomycin and its anomer using N-(triisopropylsilyl)pyrrole as a synthetic equivalent for the maleimide C3-anion

Showdomycin (1) and its anomer (2) have been prepared in four steps from readily available trichloroacetimidate 9. The key step involves reaction of the last compound with the title pyrrole 3 so as to form a chromatographically separable mixture of the pyrrole C-glycosides 10 and 11. These pyrroles are desilylated then oxidized to the corresponding maleimides using PCC.

TOTAL SYNTHESIS OF D-(+)-SHOWDOMYCIN FROM SYN-2,5-DISUBSTITUTED TETRAHYDROFURAN

D-(+)-Showdomycin, first isolated from Streptomyces showdoensis, has been synthesized starting from syn-2,5-disubstituted dihydrofuran 3.The key conversion was the functionalization of 2-thiophenylfuranyl group in 13 into maleic acid moiety in 12.