Synthesis of polyhydroxycyclohexanes and relatives from (-)-quinic acid

被引：22
|
作者：
González, C
Carballido, M
Castedo, L
机构：
[1] Univ Santiago Compostela, Fac Quim, CSIC, Dept Quim Organ, Santiago De Compostela 15782, Spain
[2] Univ Santiago Compostela, Fac Quim, CSIC, Unidad Asociada, Santiago De Compostela 15782, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 06期
关键词：
D O I：
10.1021/jo026692m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and versatile strategy for the synthesis of polyhydroxycyclohexanes and related compounds 3-6 is reported. The successful synthesis of these analogues has been achieved from a common intermediate, quinic acid derived lactone 2, rapidly accessible from cheap and commercially available (-)-quinic acid (1) as a chiral template. A practical route involving stereocontrolled epoxide formation and hydrolysis has been developed for the synthesis of 2,3-trans analogues 3 and 4. The preparation of the 2,3-cis analogues 5 and 6 has been realized by diasteroselective oxidation of a 5,6-double bond.
引用
收藏
页码：2248 / 2255
页数：8
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