141478-45-7

Upstream product

• 41977-20-2 (2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene 
• 108-88-3 toluene 

Relevant academic research and scientific papers

A model study directed towards a practical enantioselective total synthesis of (-)-morphine

A tricyclic ring system 10 containing the stereogenic centers of the nonaromatic portion of morphine (1) has been prepared in eight steps from toluene by the combination of microbial oxidation and intramolecular Diels-Alder cycloaddition followed by a Cop

Synthesis and reactions of enantiopure substituted benzene cis-hexahydro-1,2-diols

Enantiopure dis-dihydro-1,2-diol metabolites, obtained from toluene dioxygenase-catalysed dis-dihydroxylation of six monosubstituted benzene substrates, have been converted to their corresponding dis-hexahydro-1,2-diol derivatives by catalytic hydrogenation via their dis-tetrahydro-1,2-diol intermediates. Optimal reaction conditions for total catalytic hydrogenation of the dis-dihydro-1,2-diols have been established using six heterogeneous catalysts. The relative and absolute configurations of the resulting benzene dis-hexahydro-1,2-diol products have been unequivocally established by X-ray crystallography and NMR spectroscopy. Methods have been developed to obtain enantiopure dis-hexahydro-1,2diol diastereoisomers, to desymmetrise a meso-cishexahydro-1,2-diol and to synthesise 2-substituted cyclohexanols. The potential of these enantiopure cyclohexanols as chiral reagents was briefly evaluated through their application in the synthesis of two enantiomerically enriched phosphine oxides from the corresponding racemic phosphine precursors.

A comparative study of the synthesis of 3-substituted catechols using an enzymatic and a chemoenzymatic method

A series of cis-dihydrodiol metabolites, available from the bacterial dioxygenase-catalysed oxidation of monosubstituted benzene substrates using Pseudomonas putida UV4 , have been converted to the corresponding catechols using both a heterogeneous catalyst (Pd/c) and a naphthalene cis-diol dehydrogenase enzyme present in whole cells of the recombinant strain Escherichia coli DH5α(pUC129: nar B). A comparative study of the merits of both routes to 3-substituted catechols has been carried out and the two methods have been found to be complementary. A similarity in mechanism for catechol formation under both enzymatic and chemoenzymatic conditions, involving regioselective oxidation of the hydroxyl group at C-1, has been found using deuterium labelled toluene cis-dihydrodiols. The potential, of combining a biocatalytic step (dioxygenase-catalysed cis-dihydroxylation) with a chemocatalytic step (Pd/C-catalysed dehydrogenation), into a one-pot route to catechols, from the parent substituted benzene substrates, has been realised.

Chemoenzymatic synthesis of enantiopure (+)-presqualene diphosphate analogues

cis-1,2-Dihydrocatechol 2, a product of microbial oxidation of toluene, has been converted into the enantiopure analogues 24-27 of presqualene diphosphate (PSDP, 1).