The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents

Ehab S Taher; Prue Guest; Amanda Benton; Xinghua Ma; Martin G Banwell; Anthony C Willis; Tobias Seiser; Trevor W Newton; Johannes Hutzler

doi:10.1021/acs.joc.6b02372

The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents

J Org Chem. 2017 Jan 6;82(1):211-233. doi: 10.1021/acs.joc.6b02372. Epub 2016 Dec 27.

Authors

Ehab S Taher¹, Prue Guest¹, Amanda Benton¹, Xinghua Ma¹, Martin G Banwell¹, Anthony C Willis¹, Tobias Seiser², Trevor W Newton², Johannes Hutzler²

Affiliations

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
² BASF SE , Carl-Boschstrasse 38, Ludwigshafen 67056, Germany.

PMID: 28026176
DOI: 10.1021/acs.joc.6b02372

Abstract

A series of 28 analogues of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin A (1) has been synthesized through cross-couplings of various enantiomerically pure haloconduritols or certain deoxygenated derivatives with either terminal alkynes or borylated alkenes. Some of these analogues display modest herbicidal activities, and physiological profiling studies suggest that analogue 4 inhibits photosystem II in isolated thylakoids in vitro.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Araceae / drug effects*
Diterpenes / chemical synthesis
Diterpenes / chemistry
Diterpenes / pharmacology*
Herbicides / chemical synthesis
Herbicides / chemistry
Herbicides / pharmacology*
Photosystem II Protein Complex / antagonists & inhibitors*
Photosystem II Protein Complex / metabolism

Substances

Diterpenes
Herbicides
Photosystem II Protein Complex
geranylcyclohexentriol-phomentrioloxin