172877-72-4Relevant academic research and scientific papers
A Formal Approach to Xylosmin and Flacourtosides E and F: Chemoenzymatic Total Synthesis of the Hydroxylated Cyclohexenone Carboxylic Acid Moiety of Xylosmin
Ghavre, Mukund,Froese, Jordan,Murphy, Brennan,Simionescu, Razvan,Hudlicky, Tomas
, p. 1156 - 1159 (2017)
The hydroxylated cyclohexenone carboxylic acid moiety of xylosmin was synthesized in eight steps from benzoic acid. The key steps in the synthesis involved the enzymatic dihydroxylation of benzoic acid by the whole cell fermentation with Ralstonia eutroph
Palladium Catalyzed Stereoselective Arylation of Biocatalytically Derived Cyclic 1,3-Dienes: Chirality Transfer via a Heck-Type Mechanism
Dun?s, Petter,Kann, Nina,Kociok-K?hn, Gabriele,Lewis, Simon E.,Norrby, Per-Ola,Paterson, Andrew J.,Rahm, Martin
supporting information, p. 2464 - 2469 (2020/08/05)
Microbial arene oxidation of benzoic acid with Ralstonia eutropha B9 provides a chiral highly functionalized cyclohexadiene, suitable for further structural diversification. Subjecting this scaffold to a Pd-catalyzed Heck reaction effects a regio-and ster
A Chemoenzymatic Formal Synthesis of Epoxyquinols A and B
Collins, Jonathan A.,Duncan, Madeleine M.,Gerry, Christopher J.
supporting information, p. 2193 - 2197 (2019/11/25)
A formal synthesis of epoxyquinols A and B was completed in nine steps starting from benzoic acid. Enantioselectivity was established through an enzymatic arene dihydroxylation reaction performed by whole cells of Ralstonia eutropha B9 expressing benzoate
Chemoenzymatic synthesis of idesolide from benzoic acid
Adams, David R.,Aichinger, Christian,Rinner, Uwe,Hudlicky, Tomas
experimental part, p. 725 - 729 (2011/04/26)
Idesolide was synthesized in five steps from benzoic acid by base-catalyzed dimerization of hydroxy keto ester, obtained from diol, the product of the whole-cell fermentation of benzoic acid with R. eutrophus B9. Georg Thieme Verlag Stuttgart - New York.
Synthesis of a broad array of highly functionalized, enantiomerically pure cyclohexanecarboxylic acid derivatives by microbial dihydroxylation of benzoic acid and subsequent oxidative and rearrangement reactions
Myers, Andrew G.,Siegel, Dionicio R.,Buzard, Daniel J.,Charest, Mark G.
, p. 2923 - 2926 (2007/10/03)
(equation presented) We have found that the 1,2-dihydroxylation of benzoic acid with Alcaligenes eutrophus strain B9, first reported in 1971 by Reiner and Hegeman, is readily adapted for the preparation of tens to hundreds of grams of (1S,2R)-1,2-dihydrox
Synthetic application of biotransformations: absolute stereochemistry and Diels-Alder reactions of the (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid from Pseudomonas putida
Jenkins, Gareth N.,Ribbons, Douglas W.,Widdowson, David A.,Slawin, Alexandra M. Z.,Williams, David J.
, p. 2647 - 2656 (2007/10/02)
1,cis-2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid, 2, produced by Pseudomonas putide, U103, was shown via X-ray analysis of its p-bromobenzoylmethyl ester to have (1S 2R) absolute stereochemistry.The stereo- and regio-selectivity of a series of cycloadditions of the methyl ester 3 (R = Me) the methyl ester acetonide 5 and the hydroxymethylacetonide 6 (R = H) with singlet oxygen, 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione, N-phenylmaleimide and nitrosobenzene have been established.The stereochemistry of the oxygen adduct 7 of 5 was unambiguously assigned by X-ray analysis of 7.The acetonides 5 and 6 (R = H) were attacked by the dienophiles anti to the acetonide group.The diol ester 3 underwent attack on the face syn to the diol groups.The regiochemistry of the addition of nitrosobenzene was predominantly with the N-phenyl group distal to the ester function in 3 and 5, but proximal to the hydroxymethyl group in 6 (R = H).
