151622-68-3Relevant academic research and scientific papers
Palladium-catalyzed carbonylation of halo arene-cis-dihydrodiols to the corresponding carboxylates. Access to compounds unavailable by toluene dioxygenase-mediated dihydroxylation of the corresponding benzoate esters
Froese, Jordan,Hudlicky, Jason Reed,Hudlicky, Tomas
, p. 7810 - 7819 (2014/12/10)
A series of arene-cis-dihydrodiol carboxylates was prepared by palladium-catalyzed carbonylation of (1S, 2S-cis)-3-iodo-3,5-cyclohexadiene-1,2-diol, which is obtained in high titers by enzymatic dihydroxylation of iodobenzene. Both the free diol and the corresponding acetonide were subjected to this protocol to produce various arene-cis-dihydrodiol carboxylates that are unavailable by fermentation of the corresponding benzoates or are produced in low yields. The comparison of yields obtained from fermentation versus carbonylation was made for all compounds investigated. Experimental and spectral data are provided for all new compounds. This journal is
Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems
Fabris, Fabrizio,Collins, Jonathan,Sullivan, Bradford,Leisch, Hannes,Hudlicky, Tomas
scheme or table, p. 2619 - 2627 (2009/10/30)
A series of benzoate esters (methyl, ethyl, n-Pr, i-Pr, n-Bu, t-Bu, allyl, and propargyl) were subjected to enzymatic dihydroxylation by E. coli JM 109(pDTG 601) strain in a whole-cell fermentation. The cis-cyclohexadienediols were obtained in yields of ～1g/L except for n-propyl- and i-propyl benzoate which were found to be poor substrates. n-Butyl and t-butyl benzoates were not oxidized at all. The absolute stereochemistry for all metabolites was determined by comparison with a standard prepared from (1S-cis)-3-bromo-3,5- cyclohexadiene-1,2-diol, whose absolute configuration is well established. The free diols were found to be quite stable compared to other cis-dihydrodiols of this type, however, their acetonides underwent a dimerization via a regio- and stereoselective Diels-Alder cycloaddition. The diol derived from ethyl benzoate was subjected to a stereo- and regioselective inverse electron demand Diels-Alder cycloadditions with several dienophiles. The new adducts were completely characterized. The hetero-Diels-Alder reaction of this diol with an acyl nitroso dienophile yielded regio- and stereoselectively a bicyclic oxazine, which upon reduction provided a useful derivative of amino shikimate that can be exploited in an approach to oseltamivir (Tamiflu) and other amino cyclitols. The diol was also converted to carba-α-L-galactopyranose to demonstrate its potential utility as a source of pseudo sugars. Experimental and spectral data are provided for all new compounds. The Royal Society of Chemistry 2009.
Syntheses of 6β-hydroxyshikimic acid and its derivatives
Blacker, A. John,Booth, R. John,Davies, Gareth M.,Sutherland, James K.
, p. 2861 - 2870 (2007/10/02)
The conversion of (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol, (5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carbonitrile and methyl (5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate into 6β-hydroxyshikimic acid and protected derivatives is described.
