Selective deoxygenation of leurosine: concise access to anhydrovinblastine.
Straightforward access to anhydrovinblastine starting from the parent alkaloid leurosine is reported. The key deoxygenation step was first optimized on a model substrate. However, applied to leurosine, only the low-valent Cp2TiCl gave satisfactory results.
CEA/Saclay, Service de Marquage Moléculaire et de Chimie Bioorganique, Bât. 547, Département de Biologie Joliot-Curie, 91191 Gif sur Yvette Cedex, France.
Christophe
C
Hardouin
Eric
E
Doris
Bernard
B
Rousseau
Charles
C
Mioskowski
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002384:Catalysis; D030008:Catharanthus / Q000737:chemistry; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008270:Madagascar; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D014025:Titanium; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D014748:Vinca Alkaloids / Q000737:chemistry*; D000077235:Vinorelbine
D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D014748:Vinca Alkaloids; C002067:leurosine; C056817:3',4'-anhydrovinblastine; D014747:Vinblastine; D014025:Titanium; D000077235:Vinorelbine