A mild, highly selective and remarkably easy procedure for deprotection of aromatic acetates using ammonium acetate as a neutral catalyst in aqueous medium

被引:57
作者
Ramesh, C [1 ]
Mahender, G [1 ]
Ravindranath, N [1 ]
Das, B [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India
关键词
aromatic acetates; ammonium acetate; deprotection; bioactive phenolic compounds; venkatasin;
D O I
10.1016/S0040-4020(02)01635-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ammonium acetate was found to catalyze efficiently the selective deprotection of aromatic acetates in the presence of various sensitive functionalities in aqueous methanol under neutral conditions at room temperature to yield the corresponding phenols in excellent yields. The method has been utilized for deprotection of acetates of several naturally occurring bioactive phenolic compounds and for preparation of venkatasin, a natural coumarino-lignan, from the anticancer compound cleorniscosin A. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1049 / 1054
页数:6
相关论文
共 18 条
[1]   A mild procedure for rapid and selective deprotection of aryl acetates using natural kaolinitic clay as a reusable catalyst [J].
Bandgar, BP ;
Uppalla, LS ;
Sagar, AD ;
Sadavarte, VS .
TETRAHEDRON LETTERS, 2001, 42 (06) :1163-1165
[2]  
BEISSELIER VL, 1997, TETRAHEDRON LETT, V38, P2981
[3]   Selective deprotection of aryl acetates, benzoates, pivalates, and tosylates under nonhydrolytic and virtually neutral conditions [J].
Chakraborti, AK ;
Nayak, MK ;
Sharma, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :8027-8030
[4]   CHEMICAL CONSTITUENTS OF ECHITES-HIRSUTA (APOCYNACEAE) [J].
CHIEN, MM ;
SVOBODA, GH ;
SCHIFF, PL ;
SLATKIN, DJ ;
KNAPP, JE .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1979, 68 (02) :247-249
[5]   1-(2-ACETOXYETHOXY)-2,4,6-TRINITROBENZENE - A NEW SUBSTRATE FOR ENZYME CATALYZED-HYDROLYSIS [J].
CRAMPTON, MR ;
HOLT, KE ;
PERCY, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (10) :1701-1704
[6]   Venkatasin, a new coumarino-lignoid from Jatropha gossypifolia [J].
Das, B ;
Venkataiah, B ;
Kashinatham, A .
NATURAL PRODUCT LETTERS, 1999, 13 (04) :293-297
[7]  
DAS B, 1993, PHYTOCHEMISTRY, V33, P2529
[8]   DEACYLATION OF AROMATIC ACETATES - A NEW METHOD OF SELECTIVE PROTECTION OF THE HYDROXYL FUNCTION [J].
GONZALEZ, AG ;
JORGE, ZD ;
DORTA, HL ;
LUIS, FR .
TETRAHEDRON LETTERS, 1981, 22 (04) :335-336
[9]  
GREENE TW, 1995, PROTECTING GROUPS OR
[10]  
Guo Jincan, 1994, Journal of the American Chemical Society, V116, P6062, DOI 10.1021/ja00093a002