Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Org Lett. 2011 Aug 5;13(15):3790-3. doi: 10.1021/ol201252x. Epub 2011 Jun 28.
A divergent synthesis of (-)-4-epi-shikimic acid was developed. This route features a one-pot zinc-mediated reductive ring opening of an arabinofuranose followed by a Barbier reaction and culminates in a ring-closing metathesis. Functionalization of (-)-4-epi-shikimic acid via conjugate addition of a thiol occurs in high diastereoselectivity to afford a product with the features of fucosylated glycans.
开发了一种（-）-4-表-莽草酸的发散合成方法。该路线的特点是一锅法锌介导的阿拉伯呋喃糖还原开环，接着是 Barbier 反应，最后是环 closing metathesis。通过硫醇的共轭加成对（-）-4-表-莽草酸进行官能化，高非对映选择性地得到具有岩藻糖基聚糖特征的产物。
