文献类型：期刊文献

中文题名：Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates

英文题名：Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates

作者：Quan Na Nie Liangdeng Shi Xiaoxin Zhu Ruiheng Lu Xian[1]

机构：[1]Department of Pharmaceutical Engineering, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

年份：2012

卷号：30

期号：12

起止页码：2759

中文期刊名：Chinese Journal of Chemistry

外文期刊名：中国化学（英文版）

收录：CSTPCD;;Scopus;CSCD:【CSCD2011_2012】；

基金：the National Natural Science Foundation of China （No. 20972048） and Shanghai Educational Development Foundation （The Dawn Program： No. 03SG27） for the financial support of this work.

语种：英文

中文关键词：chiron; cyclic sulfite; epoxide; shikimic acid; synthesis

外文关键词：chiron; cyclic sulfite; epoxide; shikimic acid; synthesis

摘要：All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate （la--ld） are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant （--）-shikimic acid （2） via cyclic sulfite intermediates are described in this article. The targeted compound （3R,4R,5S）-la was synthesized via four steps from （--）-shikimic acid in 79% overall yield. The other three targeted compounds （3S,4R,5S）-lb, （3S,4S,5R）-1c and （3R,4S,5R）-ld were synthesized via seven steps from （--）-shikimic acid in 56%, 64% and 65% overall yields, respectively.
All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate （la--ld） are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant （--）-shikimic acid （2） via cyclic sulfite intermediates are described in this article. The targeted compound （3R,4R,5S）-la was synthesized via four steps from （--）-shikimic acid in 79% overall yield. The other three targeted compounds （3S,4R,5S）-lb, （3S,4S,5R）-1c and （3R,4S,5R）-ld were synthesized via seven steps from （--）-shikimic acid in 56%, 64% and 65% overall yields, respectively.