First efficient synthesis of chlorogenic acid

被引：4
|
作者：
Sefkow, M [1 ]
机构：
[1] Univ Potsdam, Inst ORgan Chem & Strukturanalyt, D-14476 Golm, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 2001卷 / 06期
关键词：
chlorogenic acid; natural products; acylation; acetalization; antioxidant;
D O I：
10.1002/1099-0690(200103)2001:6<1137::AID-EJOC1137>3.0.CO;2-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%. The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic acetalization protocol. Esterification of 6 with caffeic acid chloride (3) afforded ester 12. Cleavage of all the protecting groups of 12 was accomplished in one step under acidic conditions. The progress of the hydrolysis was monitored by MALDI-MS.
引用
收藏
页码：1137 / 1141
页数：5
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