Concise synthesis of anhydrovinblastine from leurosine.
[reaction: see text] The Cp(2)TiCl-mediated deoxygenation of leurosine (1) afforded anhydrovinblastine (4) in good yield. Furthermore, as the reaction proceeded via a carbon-centered radical intermediate, this transient was also trapped by a hydrogen-atom donor to afford selectively reduced alkaloid 10.
Hardouin
Christophe
C
CEA/Saclay, Service de Marquage Moléculaire et de Chimie Bioorganique, Bât. 547, Département de Biologie Joliot-Curie, 91191 Gif sur Yvette Cedex, France.
Doris
Eric
E
Rousseau
Bernard
B
Mioskowski
Charles
C
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D014025:Titanium; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D014748:Vinca Alkaloids / Q000737:chemistry*
D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D014748:Vinca Alkaloids; C002067:leurosine; D014747:Vinblastine; D014025:Titanium