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Iron(III)/NaBH 4 -Mediated Additions to Unactivated Alkenes: Synthesis of Novel 20′-Vinblastine Analogues

2012; American Chemical Society; Volume: 14; Issue: 6 Linguagem: Inglês

10.1021/ol300173v

1523-7060

Erick K. Leggans, Timothy J. Barker, Katharine K. Duncan, Dale L. Boger,

Radical Photochemical Reactions

An Fe(III)/NaBH4-mediated reaction for the functionalization of unactivated alkenes is described defining the alkene substrate scope, establishing the exclusive Markovnikov addition, exploring a range of free radical traps, examining the Fe(III) salt and initiating hydride source, introducing H2O–cosolvent mixtures, and exploring catalytic variants. Its use led to the preparation of a novel, potent, and previously inaccessible C20′-vinblastine analogue.