Chemoenzymatic total synthesis of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin

Xinghua Ma; Martin G Banwell; Anthony C Willis

doi:10.1021/np4002866

Chemoenzymatic total synthesis of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin

J Nat Prod. 2013 Aug 23;76(8):1514-8. doi: 10.1021/np4002866. Epub 2013 Jul 29.

Authors

Xinghua Ma¹, Martin G Banwell, Anthony C Willis

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.

PMID: 23895674
DOI: 10.1021/np4002866

Abstract

The enantiomeric form, 1R, of the structure (1S) assigned to the phytotoxic natural product phomentrioloxin has been synthesized in seven steps from the homochiral cis-1,2-dihydrocatechol 3. These studies reveal that the true structure of phomentrioloxin is represented by 1R and not by 1S.

Publication types

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

MeSH terms

Alkaloids / chemistry
Biological Factors / chemical synthesis*
Biological Factors / chemistry
Biological Factors / pharmacology
Cyclohexanols / chemical synthesis*
Cyclohexanols / chemistry
Cyclohexanols / pharmacology
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / pharmacology
Molecular Structure
Stereoisomerism

Substances

Alkaloids
Biological Factors
Cyclohexanols
Diterpenes
geranylcyclohexentriol-phomentrioloxin
phomentrioloxin