10′-Fluorovinblastine and 10′-fluorovincristine: synthesis of a key series of modified Vinca alkaloids

H Gotoh, KK Duncan, WM Robertson…

Index: Gotoh, Hiroaki; Duncan, Katharine K.; Robertson, William M.; Boger, Dale L. ACS Medicinal Chemistry Letters, 2011 , vol. 2, # 12 p. 948 - 952

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Citation Number: 30

Abstract

A study on the impact of catharanthine C10 and C12 indole substituents on the biomimetic Fe (III)-mediated coupling with vindoline led to the discovery and characterization of two new and substantially more potent derivatives, 10′-fluorovinblastine and 10′-fluorovincristine. In addition to defining a pronounced and unanticipated substituent effect on the biomimetic coupling, fluorine substitution at C10′, which minimally alters the natural products, was ...