Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

被引：35

作者：

Freeman, David B. ^{[1
]}

Holubec, Alexandra A. ^{[1
]}

Weiss, Matthew W. ^{[1
]}

Dixon, Julie A. ^{[1
]}

Kakefuda, Akio ^{[1
]}

Ohtsuka, Masami ^{[1
]}

Inoue, Munenori ^{[1
]}

Vaswani, Rishi G. ^{[1
]}

Ohki, Hidenori ^{[1
]}

Doan, Brian D. ^{[1
]}

Reisman, Sarah E. ^{[1
]}

Stoltz, Brian M. ^{[1
]}

Day, Joshua J. ^{[1
]}

Tao, Ran N. ^{[1
]}

Dieterich, Noah A. ^{[1
]}

Wood, John L. ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 33期

关键词：

Welwitindolinone; 3+2] Dipolar cycloaddition; Rhodium carbenoid; O-H insertion; Chloronium-ion semi-pinacol; INITIATED CLAISEN REARRANGEMENT; MULTIPLE-DRUG RESISTANCE; (+/-)-WELWITINDOLINONE-A ISONITRILE; EFFICIENT SYNTHESIS; WELWISTATIN; CYCLIZATION; OXIDATION; FISCHERINDOLES; ISOXAZOLIDINES; HAPALINDOLES;

D O I：

10.1016/j.tet.2010.04.131

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O-H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6647 / 6655

页数：9

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