De Novo Asymmetric Synthesis and Biological Analysis of the Daumone Pheromones in Caenorhabditis elegans and in the Soybean Cyst Nematode Heterodera glycines.

Abstract

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 C. elegans and for effects on hatching of the related nematode H. glycines. This data provides additional structure activity relationships (SAR) that further inform the study of nematode signaling.

• Authors: Haibing Guo, James J La Clair, Edward P Masler, George O'Doherty, Yalan Xing
• Journal: Tetrahedron (Tetrahedron) Vol. 72 Issue 18 Pg. 2280-2286 (May 05 2016) ISSN: 0040-4020 [Print] England
• PMID: 29445247 (Publication Type: Journal Article)