Iron(III)/NaBH4-Mediated Additions to Unactivated Alkenes: Synthesis of Novel 20′-Vinblastine Analogues

被引：253
作者：
Leggans, Erick K.
Barker, Timothy J.
Duncan, Katharine K.
Boger, Dale L. [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 06期
关键词：
ASYMMETRIC TOTAL-SYNTHESIS; ROSEUS G-DON; VINCA-ROSEA; KEY SERIES; BOROHYDRIDE REDUCTION; VINBLASTINE ANALOGS; SODIUM-BOROHYDRIDE; MOLECULAR-OXYGEN; NATURAL-PRODUCTS; OLEFINS;
D O I：
10.1021/ol300173v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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页码：1428 / 1431
页数：4
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