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

TETRAHEDRON

卷:72

Article

Guo, Haibing¹  La Clair, James J.²  Masler, Edward P.³  O'Doherty, George A.⁴  Xing, Yalan⁵ 

[1] Hubei Univ Sci & Technol, Sch Nucl Technol & Chem & Life Sci, Xianning 437100, Peoples R China

[2] Xenobe Res Inst, POB 3052, San Diego, CA 92163 USA

[3] ARS, Nematol Lab, USDA, NEA, Beltsville, MD 20705 USA

[4] Northeastern Univ, Dept Chem & Chem Biol, Boston, MA 02115 USA

[5] William Paterson Univ, Dept Chem, 300 Pompton Rd, Wayne, NJ 07470 USA

关键词: Daumone pheromones;    De novo asymmetric synthesis;    Dauer activity;    Hatching effect;    Pd-glycosylation;   

DOI  :  10.1016/j.tet.2016.03.033

来源: Elsevier

【 摘 要 】

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 stereo chemistry 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. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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