An epiisopicropodophyllin aza analogue via palladium-catalyzed pseudo-domino cyclization.
A new aza analogue of epiisopicropodophyllin (the C-3 epimer of podophyllotoxin) has been synthesized exploiting two original strategic steps. Rings A/B and E are entered at an early stage via a cationic benzhydrylation process. A palladium-catalyzed pseudo-domino (Pd-PDOM) intramolecular process generates rings C/D in a single synthetic operation.
Poli
Giovanni
G
UMR 7611 CNRS, Université Pierre et Marie Curie, 4 Place Jussieu, Tour 44-45, Boîte 183, F-75252, Paris, Cedex 05, France. poli@ccr.jussieu.fr
Giambastiani
Giuliano
G
D001372:Aza Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D005047:Etoposide / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011034:Podophyllotoxin / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001372:Aza Compounds; D007202:Indicators and Reagents; D010165:Palladium; D005047:Etoposide; D011034:Podophyllotoxin