Synthesis of methoxy and hydroxy containing tetralones: versatile intermediates for the preparation of biologically relevant molecules

被引:18
作者
Ghatak, A
Dorsey, JM
Garner, CM
Pinney, KG
机构
[1] Baylor Univ, Dept Chem & Biochem, Waco, TX 76798 USA
[2] Baylor Univ, Ctr Drug Discovery, Waco, TX 76798 USA
关键词
D O I
10.1016/S0040-4039(03)00715-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 5-hydroxy-6-methoxy-1-tetralone and the 7-hydroxy regioisomer along with the corresponding 5,7-dihydroxy analog has been achieved using an efficient directed metallation procedure followed by a regioselective methylene oxidation. This methodology represents a general synthetic route for the preparation of highly oxygenated tetralone analogs which are versatile building blocks for the construction of molecules of biological interest. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4145 / 4148
页数:4
相关论文
共 15 条
[1]   THE TERTIARY AMIDE AS AN EFFECTIVE DIRECTOR OF ORTHO LITHIATION [J].
BEAK, P ;
BROWN, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :34-46
[2]   The development of combretastatin A4 phosphate as a vascular targeting agent [J].
Chaplin, DJ ;
Hill, SA .
INTERNATIONAL JOURNAL OF RADIATION ONCOLOGY BIOLOGY PHYSICS, 2002, 54 (05) :1491-1496
[3]   Synthesis and in vitro antibacterial activities of novel conformationally restricted hygromycin A analogues [J].
Cooper, CB ;
Blair, KT ;
Jones, CS ;
Minich, ML .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (13) :1747-1752
[4]  
DAY WW, 2001, Patent No. 0177093
[6]  
GHATAK A, 2001, 222 AM CHEM SOC NAT
[7]   2-(3-tert-butyldimethylsiloxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)indole [J].
Hadimani, MB ;
Kessler, RJ ;
Kautz, JA ;
Ghatak, A ;
Shirali, AR ;
O'Dell, H ;
Garner, CM ;
Pinney, KG .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2002, 58 (06) :O330-O332
[8]   Facile synthesis of 5,6-dimethoxy-1-tetralone [J].
Lahiri, S ;
Ramarao, C ;
Rao, BV ;
Rao, AVR ;
Chorghade, MS .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (01) :71-72
[9]   MAMMALIAN ANTIFERTILITY AGENTS .6. A NOVEL SEQUENCE FOR PREPARATION OF 1,2-DISUBSTITUTED 3,4-DIHYDRONAPHTHALENES [J].
LEDNICER, D ;
EMMERT, DE ;
LYSTER, SC ;
DUNCAN, GW .
JOURNAL OF MEDICINAL CHEMISTRY, 1969, 12 (05) :881-&
[10]   DIELS-ALDER REACTIVITY OF PYRANO[3,4-B]INDOL-3-ONES .4. SYNTHESIS OF THE CARBAZOLE ALKALOIDS CARBAZOMYCIN-A AND CARBAZOMYCIN-B AND HYELLAZOLE [J].
MOODY, CJ ;
SHAH, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2463-2471