通过烯-二烯交叉复分解反应选择性合成(2Z,4E)-二烯基酯。
Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis.
作者信息
Moura-Letts Gustavo, Curran Dennis P
机构信息
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
出版信息
Org Lett. 2007 Jan 4;9(1):5-8. doi: 10.1021/ol062017d.
Abstract
[reaction: see text] Cross metathesis of terminal alkenes with methyl (2Z,4E)-hexadienoate and related dienyl esters provides substituted (2Z,4E)-dienyl esters in good yields. Small-scale reactions are effectively promoted by the standard second-generation Grubbs-Hoveyda catalyst (GH-II), while a new fluorous GH-II catalyst is used for separation and recovery in gram-scale reactions. The transformation is featured in a rapid synthesis of the bottom fragments of the potent anticancer agents (-)-dictyostatin and 6-epi-dictyostatin.
摘要
[反应：见正文] 末端烯烃与甲基(2Z,4E)-己二烯酸酯及相关二烯基酯的交叉复分解反应能以良好产率提供取代的(2Z,4E)-二烯基酯。小规模反应能被标准的第二代格拉布催化剂（GH-II）有效促进，而一种新型氟代GH-II催化剂用于克级反应中的分离和回收。该转化反应的特点是能快速合成强效抗癌药物(-)-网抑素和6-表-网抑素的底部片段。
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