TiCl4-Promoted Tandem Carbonyl or Imine Addition and Friedel-Crafts Cyclization: Synthesis of Benzo-Fused Oxabicyclooctanes and Nonanes

被引：12
作者：
Ghosh, Arun K. [1 ]
Martyr, Cuthbert D.
Xu, Chun-Xiao
机构：
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 08期
基金：
美国国家卫生研究院;
关键词：
COMPONENT COUPLING REACTION; FACILE;
D O I：
10.1021/ol300494q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and convenient synthesis of benzo-fused 8-oxabicyclo[3.2.1]octane and 9-oxabicyclo[4.2.1]nonane derivatives are described. The reaction involved a TiCl4-mediated tandem carbonyl or imine addition followed by a Friedel-Crafts cyclization to provide these functionalized derivatives in good to excellent yields and high diastereoselectivity.
引用
收藏
页码：2002 / 2005
页数：4
相关论文
共 27 条
[1]   An Expeditious Synthesis of Bruguierol A [J].
Fananas, Francisco J. ;
Fernandez, Amadeo ;
Cevic, Deniz ;
Rodriguez, Felix .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) :932-934
[2]  
Ghosh A. K., 2009, PCT Int. appl., Patent No. [WO 2009091941 A1 20090723, 2009091941]
[3]  
Ghosh A.K., 2012, ANGEW CHEM INT EDIT, V51, P2
[4]   TiCl4 promoted three component coupling reaction:: A new method for the synthesis of functionalized tetrahydrofurans and tetrahydropyrans [J].
Ghosh, AK ;
Kawahama, R .
TETRAHEDRON LETTERS, 1999, 40 (06) :1083-1086
[5]   Stereoselective construction of quaternary carbon centers by three component coupling reactions [J].
Ghosh, AK ;
Kawahama, R ;
Wink, D .
TETRAHEDRON LETTERS, 2000, 41 (44) :8425-8429
[6]   TiCl4-promoted multicomponent reaction:: A new entry to functionalized α-amino acids [J].
Ghosh, AK ;
Xu, CX ;
Kulkarni, SS ;
Wink, D .
ORGANIC LETTERS, 2005, 7 (01) :7-10
[7]   TiCl4 promoted three component coupling reaction:: an efficient method for the substituted tetrahydropyrilidene acetates [J].
Ghosh, AK ;
Kawahama, R .
TETRAHEDRON LETTERS, 1999, 40 (26) :4751-4754
[8]   A short synthesis of (±)-eburnamonine [J].
Ghosh, AK ;
Kawahama, R .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5433-5435
[9]   Asymmetric multicomponent reactions: Diastereoselective synthesis of substituted pyrrolidines and prolines [J].
Ghosh, Arun K. ;
Kulkarni, Sarang ;
Xu, Chun-Xiao ;
Fanwick, Phillip E. .
ORGANIC LETTERS, 2006, 8 (20) :4508-4511
[10]   A Stereoselective Synthesis of (-)-Viridiofungin A Utilizing a TiCl4-Promoted Asymmetric Multicomponent Reaction [J].
Ghosh, Arun K. ;
Kass, Jorden .
ORGANIC LETTERS, 2012, 14 (02) :510-512
123