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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