title: The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents.
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.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
authors.forename: Ehab S
authors.initials: ES
authors.lastname: Taher
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
authors.forename: Prue
authors.initials: P
authors.lastname: Guest
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
authors.forename: Amanda
authors.initials: A
authors.lastname: Benton
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
authors.forename: Xinghua
authors.initials: X
authors.lastname: Ma
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
authors.forename: Martin G
authors.identifier: 0000-0002-0582-475X
authors.initials: MG
authors.lastname: Banwell
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
authors.affiliation: BASF SE , Carl-Boschstrasse 38, Ludwigshafen 67056, Germany.
authors.forename: Tobias
authors.initials: T
authors.lastname: Seiser
authors.affiliation: BASF SE , Carl-Boschstrasse 38, Ludwigshafen 67056, Germany.
authors.forename: Trevor W
authors.initials: TW
authors.lastname: Newton
authors.affiliation: BASF SE , Carl-Boschstrasse 38, Ludwigshafen 67056, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Hutzler
mesh_terms: D029064:Araceae / Q000187:drug effects*; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045332:Photosystem II Protein Complex / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D004224:Diterpenes; D006540:Herbicides; D045332:Photosystem II Protein Complex; C584602:geranylcyclohexentriol-phomentrioloxin