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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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.

Original language	English
Pages (from-to)	211-233
Number of pages	23
Journal	Journal of Organic Chemistry
Volume	82
Issue number	1
DOIs	https://doi.org/10.1021/acs.joc.6b02372
Publication status	Published - 6 Jan 2017

Access to Document

10.1021/acs.joc.6b02372

Cite this

@article{920d904fb1ab4f759d2f10ee0885ca8a,

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.",

author = "Taher, {Ehab S.} and Prue Guest and Amanda Benton and Xinghua Ma and Banwell, {Martin G.} and Willis, {Anthony C.} and Tobias Seiser and Newton, {Trevor W.} and Johannes Hutzler",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2017",

month = jan,

day = "6",

doi = "10.1021/acs.joc.6b02372",

language = "English",

volume = "82",

pages = "211--233",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents

AU - Taher, Ehab S.

AU - Guest, Prue

AU - Benton, Amanda

AU - Ma, Xinghua

AU - Banwell, Martin G.

AU - Willis, Anthony C.

AU - Seiser, Tobias

AU - Newton, Trevor W.

AU - Hutzler, Johannes

PY - 2017/1/6

Y1 - 2017/1/6

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85018514419&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.6b02372

DO - 10.1021/acs.joc.6b02372

M3 - Article

SN - 0022-3263

VL - 82

SP - 211

EP - 233

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this