171296-56-3

Upstream product

• 71277-13-9 3,4,5-trimethoxycinnamaldehyde 
• 477-67-8 picropodophyllic acid 
• 518-28-5 podofilox 
• 78216-03-2 (5R,6S,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 171483-26-4 (-)-(1R,2S)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-1,2-dihydro-3-naphthalenecarbaldehyde 
• 199996-63-9 (5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 199996-64-0 [(5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol 

Relevant academic research and scientific papers

First total synthesis of (+)-podophyllic aldehydes

The first total synthesis of three (+)-podophyllic aldehydes was achieved in a highly enantiocontrolled manner. Key steps include the organocatalyzed highly enantioselective cyclopropanation and Lewis acid-mediated chiral transfer ring expansion with exce

Synthesis and antineoplastic activity of cyclolignan aldehydes

Several aldehydes related to methyl 9-deoxy-9-oxo-α- apopicropodophyllate, a selective antitumour agent against the HT-29 colon carcinoma, have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28). All of them lacked the lactone ring but maintained their cytotoxicity at, or under, the μM level. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

Several cyclolignans lacking of the Iactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the 3 aldehyde 9 (methyl 9-deoxy-9-oxo-α-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the correspnding saturated aldehyde 13 in comparison with podophyllotoxin.