491580-75-7

Upstream product

• 491580-73-5 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin 
• 491580-65-5 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin 
• 491580-69-9 5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-9-hydroxymethyl-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 491580-64-4 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-podophyllotoxone 
• 491580-71-3 (5R,5aR,8aR,9R)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-hydroxymethyl-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 118356-07-3 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin 
• 501-53-1 benzyl chloroformate 
• 6559-91-7 4'-demethylepipodophyllotoxin 

Relevant academic research and scientific papers

Hemi-synthesis and biological activity of new analogues of podophyllotoxin

Various 4-analogues of podophyllotoxin and epipodophyllotoxin were obtained via the formation of the corresponding 4-keto derivatives. Methyloximation of podophyllotoxone, followed by subsequent catalytic hydrogenation, gave stereoselective access to 4-α-amino-4-deoxypodophyllotoxin and from there, to the corresponding acetamido and formamido derivatives. Base-catalyzed isomerisation of 4-α-amino-4-deoxypodophyllotoxin led to the corresponding picropodophyllin isomer while the 4-β-amino afforded a neopodophyllotoxin-like derivative. On the other hand, oxirane and hydroxymethyl-containing analogues were prepared from podophyllotoxin and 4-epi-4′-demethyl-podophyllotoxin, using a Takai olefination strategy. In the latter series, carboxaldehyde- and carboxylic acid-containing derivatives were also synthesized.