Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide

详细信息	查看全文 | 推荐本文 |

• 作者：Akira Morita ; Shigefumi Kuwahara
• 关键词：Elaiolide ; Cross-metathesis ; Enantioselective synthesis ; Antibiotic ; 2 ; 4-Alkadienoic acid
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：30 April 2007
• 卷：48
• 期：18
• 页码：3163-3166
• 文件大小：173 K

摘要

A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown’s asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.