De novo asymmetric synthesis and biological analysis of the daumone pheromones in Caenorhabditis elegans and in the soybean cyst nematode Heterodera glycines

详细信息    查看全文

• 作者：Haibing Guo^a ; James J. La Clair^b ; Edward P. Masler^c ; George A. O'Doherty^d ; ^{g.odoherty@neu.edu" class="auth_mail" title="E-mail the corresponding author} ; Yalan Xing^e ; ^{XINGY@wpunj.edu" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Daumone pheromones ; De novo asymmetric synthesis ; Dauer activity ; Hatching effect ; Pd-glycosylation
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：5 May 2016
• 年：2016
• 卷：72
• 期：18
• 页码：2280-2286
• 全文大小：935 K

文摘

The de novo asymmetric total syntheses of daumone 1, daumone 3 along with 5 new analogs are described. The key steps of our approach are: the diastereoselective palladium catalyzed glycosylation reaction; the Noyori reduction of 2-acetylfuran and an ynone, which introduce the absolute stereochemistry of the sugar and aglycon portion of daumone; and an Achmatowicz rearrangement, an epoxidation and a ring opening installing the remaining asymmetry of daumone. The synthetic daumones 1 and 3 as well as related analogs were evaluated for dauer activity in Caenorhabditis elegans and for effects on hatching of the related nematode Heterodera glycines. This data provides additional structure activity relationships (SAR) that further inform the study of nematode signaling.