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Scalable total synthesis and comprehensive structure-activity relationship studies of the phytotoxin coronatine.

ABSTRACT: Natural phytotoxins are valuable starting points for agrochemical design. Acting as a jasmonate agonist, coronatine represents an attractive herbicidal lead with novel mode of action, and has been an important synthetic target for agrochemical development. However, both restricted access to quantities of coronatine and a lack of a suitably scalable and flexible synthetic approach to its constituent natural product components, coronafacic and coronamic acids, has frustrated development of this target. Here, we report gram-scale production of coronafacic acid that allows a comprehensive structure-activity relationship study of this target. Biological assessment of a >120 member library combined with computational studies have revealed the key determinants of potency, rationalising hypotheses held for decades, and allowing future rational design of new herbicidal leads based on this template.

SUBMITTER: Littleson MM 

PROVIDER: S-EPMC5856746 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Scalable total synthesis and comprehensive structure-activity relationship studies of the phytotoxin coronatine.

Littleson Mairi M MM   Baker Christopher M CM   Dalençon Anne J AJ   Frye Elizabeth C EC   Jamieson Craig C   Kennedy Alan R AR   Ling Kenneth B KB   McLachlan Matthew M MM   Montgomery Mark G MG   Russell Claire J CJ   Watson Allan J B AJB  

Nature communications 20180316 1

Natural phytotoxins are valuable starting points for agrochemical design. Acting as a jasmonate agonist, coronatine represents an attractive herbicidal lead with novel mode of action, and has been an important synthetic target for agrochemical development. However, both restricted access to quantities of coronatine and a lack of a suitably scalable and flexible synthetic approach to its constituent natural product components, coronafacic and coronamic acids, has frustrated development of this ta  ...[more]

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