A concise synthesis of pinellic acid using a cross-metathesis approach
A concise synthesis of pinellic acid using a cross-metathesis approach
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DOI：
10.1016/j.tet.2009.02.063
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发表时间：
2009-04-25
期刊：
影响因子：
2.1
通讯作者：
Kuwahara, Shigefumi
中科院分区：
文献类型：
--
作者：
Miura, Ayako;Kuwahara, Shigefumi
以末端烯烃中间体间的交叉复分解反应为关键步骤，完成了对映选择性合成松油酸的新方法。松油酸是一种三羟基不饱和脂肪酸，可作为流感疫苗的口服佐剂。该合成是迄今为止最短的，从容易获得的已知二羟基酯仅通过七个步骤以17%的总产率提供了半夏酸。(C)2009爱思唯尔有限公司保留所有权利。
A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester. (C) 2009 Elsevier Ltd. All rights reserved.