Investigating the Structure–Activity Relationship of the Insecticidal Natural Product Rocaglamide

Authors

  • Roger G. Hall Syngenta Crop Protection AG Research Chemistry WST-810.3.18 CH-4332 Stein, Switzerland. roger_g.hall@syngenta.com
  • Ian Bruce Formerly Ciba Central Research, later Novartis Central Research laboratories, Macclesfield, UK
  • Nigel G. Cooke Formerly Ciba Central Research, later Novartis Central Research laboratories, Macclesfield, UK
  • Louis J. Diorazio Formerly Ciba Central Research, later Novartis Central Research laboratories, Macclesfield, UK
  • Fredrik Cederbaum Syngenta Crop Protection AG Research Chemistry WST-810.3.18 CH-4332 Stein, Switzerland
  • Markus R. Dobler Formerly Novartis Crop Protection, Basel, Switzerland
  • Ed Irving Formerly Ciba Central Research, later Novartis Central Research laboratories, Macclesfield, UK

DOI:

https://doi.org/10.2533/chimia.2017.845

Keywords:

Insecticide, Rocaglamide, Structure–activity relationship

Abstract

The natural product Rocaglamide (1), isolated from the tree Aglaia elliptifolia, is a compelling but also challenging lead structure for crop protection. In laboratory assays, the natural product shows highly interesting insecticidal activity against chewing pests and beetles, but also phytotoxicity on some crop plants. Multi-step syntheses with control of stereochemistry were required to probe the structure–activity relationship (SAR), and seek simplified analogues. After a significant research effort, just two areas of the molecule were identified which allow modification whilst maintaining activity, as will be highlighted in this paper.
CHIMIA Vol. 71 No. 12 (2017): Natural Products: Source of Innovation

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Published

2017-12-01

Issue

Vol. 71 No. 12 (2017): Natural Products: Source of Innovation

Section

Scientific Articles

License

Copyright (c) 2017 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
R. G. Hall, I. Bruce, N. G. Cooke, L. J. Diorazio, F. Cederbaum, M. R. Dobler, E. Irving, Chimia 2017, 71, 845, DOI: 10.2533/chimia.2017.845.