Design and Synthesis of Natural Product Mevalocidin Chiral Center Based Analogues

doi:10.6023/cjoc201710023

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 840-845.DOI: 10.6023/cjoc201710023 Previous Articles Next Articles

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基于天然产物Mevalocidin手性中心的结构类似物的设计与合成

吴琼友^a, 张锐^a, 潘金环^a, John Clough^b, 顾玉成^b, 杨光富^a

a 华中师范大学化学学院农药与生物教育部重点实验室武汉 430079;
b Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom

收稿日期:2017-10-21 修回日期:2017-11-24 发布日期:2017-12-15
通讯作者: 吴琼友, 杨光富 E-mail:qywu@mail.ccnu.edu.cn;gfyang@mail.ccnu.edu.cn
基金资助:
国家自然科学基金（No.21472063）资助项目.

Design and Synthesis of Natural Product Mevalocidin Chiral Center Based Analogues

Wu Qiongyou^a, Zhang Rui^a, Pan Jinhuan^a, Clough John^b, Gu Yucheng^b, Yang Guangfu^a

a Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079;
b Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire RG426 EY, United Kingdom

Received:2017-10-21 Revised:2017-11-24 Published:2017-12-15
Contact: 10.6023/cjoc201710023 E-mail:qywu@mail.ccnu.edu.cn;gfyang@mail.ccnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21472063).

1. Design and Synthesis of Natural Product Mevalocidin Chiral Center Based Analogues.PDF(506KB)

Abstract

Mevalocidin is a phytotoxin, produced by two fungal isolates designated Rosellinia DA092917 and Fusarium DA056446, and has a broad spectrum of post emergence herbicidal activity at relatively high rate (4 kg/ha). Structural modification of mevalocidin at its chiral center was investigated with the aim of discovering of novel herbicides with improved activity. In order to determine the role of hydroxyl and methyl groups of mevalocidin exhibiting the herbicidal activity, we designed (±)-deoxy-mevalocidin (1) and (±)-demethyl-mevalocidin (2), respectively. These two designed compounds were synthesized (racemate) through two different synthetic approaches and characterized by ¹H NMR, ¹³C NMR and HRMS spectra. The herbicidal activities of the synthesized compounds were evaluated against both dicotyledon and monocotyledon weeds. Bioassay results indicated that the both synthesized analogues lost the herbicidal activity when compared to parent and it demonstrated that methyl and/or hydroxyl groups at the chiral center of mevalocidin are crucial for its herbicidal activity. Thus, this study will provide insights into the structural modification of mevalocidin.

Key words: natural product, mevalocidin, chiral center, structural modification, herbicidal activity

Cite this article

Wu Qiongyou, Zhang Rui, Pan Jinhuan, Clough John, Gu Yucheng, Yang Guangfu. Design and Synthesis of Natural Product Mevalocidin Chiral Center Based Analogues[J]. Chin. J. Org. Chem., 2018, 38(4): 840-845.

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基于天然产物Mevalocidin手性中心的结构类似物的设计与合成

Design and Synthesis of Natural Product Mevalocidin Chiral Center Based Analogues

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