Design, Synthesis and Biological Evaluation of Strigolactone and Strigolactam Derivatives for Potential Crop Enhancement Applications in Modern Agriculture

Authors

  • Alain De Mesmaeker Syngenta Crop Protection AG, Crop Protection Research, Schaffhausenstrasse 101, CH-4332 Stein, Switzerland;, Email: alain.de_mesmaeker@syngenta.com
  • Claudio Screpanti Syngenta Crop Protection AG, Crop Protection Research, Schaffhausenstrasse 101, CH-4332 Stein, Switzerland
  • Raymonde Fonné-Pfister Syngenta Crop Protection AG, Crop Protection Research, Schaffhausenstrasse 101, CH-4332 Stein, Switzerland
  • Mathilde Lachia Syngenta Crop Protection AG, Crop Protection Research, Schaffhausenstrasse 101, CH-4332 Stein, Switzerland
  • Alexandre Lumbroso Syngenta Crop Protection AG, Crop Protection Research, Schaffhausenstrasse 101, CH-4332 Stein, Switzerland
  • Harro Bouwmeester Plant Hormone Biology group, Swammerdam Institute for Life Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, the Netherlands

DOI:

https://doi.org/10.2533/chimia.2019.549

PMID:

31431215

Keywords:

Crop enhancement, Keteneiminium salts, Seed germination, Strigolactones, Total synthesis

Abstract

Strigolactones have been known as signaling molecules in the rhizosphere of plants since more than 50 years. However, their roles as phytohormone have been only recognized since 2008. We describe here a very efficient synthetic access to representative canonical strigolactones displaying the A-B-C-D tetracyclic structure and to non-canonical strigolactones as carlactonoic acid and methyl carlactonoate. In addition, we report the design and the synthesis of strigolactams as promising derivatives of strigolactones for potential use in modern agriculture. Among the synthetic methods developed for this project, the intramolecular [2+2] cycloaddition of keteneiminium salts to C=C bond has been particularly useful to the synthesis of natural strigolactones and their potentially improved analogues.

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Published

2019-08-21

How to Cite

[1]
A. De Mesmaeker, C. Screpanti, R. Fonné-Pfister, M. Lachia, A. Lumbroso, H. Bouwmeester, Chimia 2019, 73, 549, DOI: 10.2533/chimia.2019.549.