Photocatalytic aerobic oxidation/semipinacol rearrangement sequence: a concise route to the core of pseudoindoxyl alkaloids

被引：93
作者：
Ding, Wei [1 ]
Zhou, Quan-Quan [1 ]
Xuan, Jun [1 ]
Li, Tian-Ren [1 ]
Lu, Liang-Qiu [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300000, Peoples R China
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 33期
基金：
中国国家自然科学基金;
关键词：
Aerobic oxidation; 2,2-Disubstituted indolin-3-one; Semipinacol rearrangement; Photocatalysis; LIGHT PHOTOREDOX CATALYSIS; C-BOND-CLEAVAGE; VISIBLE-LIGHT; SINGLET-OXYGEN; MOLECULAR-OXYGEN; SYNTHETIC ROUTE; OXIDATION; INDOLES; EFFICIENT; ALDEHYDES;
D O I：
10.1016/j.tetlet.2014.06.102
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible light-induced photocatalytic aerobic oxidation/semipinacol rearrangement has been successfully developed. This methodology allows for efficient conversion of a wide range of indoles into the synthetically significant 2,2-disubstituted indolin-3-ones, the core structure of pseudoindoxyl alkaloids, under mild reaction conditions. (C) 2014 Published by Elsevier Ltd.
引用
收藏
页码：4648 / 4652
页数：5
相关论文
共 57 条
[1]   A concise synthesis of d,l-brevianamide B via a biomimetically-inspired IMDA construction [J].
Adams, Luke A. ;
Valente, Meriah W. N. ;
Williams, Robert M. .
TETRAHEDRON, 2006, 62 (22) :5195-5200
[2]   Visible Light-Induced Aerobic Oxyamidation of Indoles: A Photocatalytic Strategy for the Preparation of Tetrahydro-5H-indolo[2,3-b]quinolinols [J].
An, Jing ;
Zou, You-Quan ;
Yang, Qing-Qing ;
Wang, Qiang ;
Xiao, Wen-Jing .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) :1483-1489
[3]  
Anju T., 2014, PHOTOCHEM PHOTOBIOL, V13, P281
[4]   A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization [J].
Baran, PS ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7904-7905
[5]   Enantioselective total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A, and their unnatural enantiomers [J].
Boger, DL ;
McKie, JA ;
Nishi, T ;
Ogiku, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) :2301-2302
[6]   Redox Economy in Organic Synthesis [J].
Burns, Noah Z. ;
Baran, Phil S. ;
Hoffmann, Reinhard W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867
[7]   ELECTROPHILIC IPSO-SUBSTITUTIONS .3. REACTIONS OF 3-SUBSTITUTED INDOLES, 4-SUBSTITUTED N,N-DIMETHYLANILINES, AND 1-SUBSTITUTED AND 3-SUBSTITUTED INDOLIZINES WITH NITROUS-ACID [J].
COLONNA, M ;
GRECI, L ;
POLONI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (02) :165-169
[8]   Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones [J].
Dalpozzo, Renato ;
Bartoli, Giuseppe ;
Bencivenni, Giorgio .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (21) :7247-7290
[9]   Photosensitized singlet oxygen and its applications [J].
DeRosa, MC ;
Crutchley, RJ .
COORDINATION CHEMISTRY REVIEWS, 2002, 233 :351-371
[10]   REACTION OF SINGLET OXYGEN WITH OLEFINS - QUESTION OF MECHANISM [J].
FRIMER, AA .
CHEMICAL REVIEWS, 1979, 79 (05) :359-387
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