154333-40-1Relevant academic research and scientific papers
Enzyme-catalysed synthesis and absolute configuration assignments of cis-dihydrodiol metabolites from 1,4-disubstituted benzenes
Boyd, Derek R.,Sharma, Narain D.,Coen, Gerard P.,Gray, Peter J.,Malone, John F.,Gawronski, Jacek
, p. 5804 - 5811 (2008/02/13)
A series of ten cis-dihydrodiol metabolites has been obtained by bacterial biotransformation of the corresponding 1,4-disubstituted benzene substrates using Pseudomonas putida UV4, a source of toluene dioxygenase (TDO). Their enantiomeric excess (ee) values have been established using chiral stationary phase HPLC and 1H NMR spectroscopy. Absolute con_figurations of the majority of cis-dihydrodiols have been established using stereochemical correlation and X-ray crystallography and the remainder have been tentatively assigned using NMR spectroscopic methods but finally confirmed by circular dichroism (CD) spectroscopy. These configurational assignments support and extend the validity of an empirical model, previously used to predict the preferred stereochemistry of TDO-catalysed cis-dihydroxylation of ten 1,4-disubstituted benzene substrates, to more than twenty-five examples.
Total syntheses of ent-conduramine A and ent-7-deoxypancratistatin
Akguen, Huelya,Hudlicky, Tomas
, p. 3081 - 3084 (2007/10/03)
The first total synthesis of the title alkaloid has been accomplished in fourteen steps form 1-bromo-4-iodobenzene or 1-fluoro-4-iodobenzene via chemoenzymatic production of the antipedal cis-diene diols 4.
Enantioselective Bacterial Biotransformation Routes to cis-Diol Metabolites of Monosubstituted Benzenes, Naphthalene and Benzocycloalkenes of Either Absolute Configuration
Allen, Christopher C. R.,Boyd, Derek R.,Dalton, Howard,Sharma, Narain D.,Brannigan, Ian,et al.
, p. 117 - 118 (2007/10/02)
Enzyme-catalysed kinetic resolution and asymmetric dihydroxylation routes to enantiopure cis-diol metabolites of arenes and benzocycloalkenes of either absolute configuration have been developed using appropriate strains of the bacterium Pseudomonas putida.
