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Author Jordan Froese


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Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin.

Daler Baidilov, Lukas Rycek, John F Trant, Jordan Froese, Brennan Murphy, Tomas Hudlicky,

Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, ... Read more >>

Angew Chem Int Ed Engl (Angewandte Chemie (International ed. in English))
[2018, 57(34):10994-10998]

Cited: 1 time

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Discovery of human cell selective effector molecules using single cell multiplexed activity metabolomics.

David C Earl, P Brent Ferrell, Nalin Leelatian, Jordan T Froese, Benjamin J Reisman, Jonathan M Irish, Brian O Bachmann,

Discovering bioactive metabolites within a metabolome is challenging because there is generally little foreknowledge of metabolite molecular and cell-targeting activities. Here, single-cell response profiles and primary human tissue comprise a response platform used to discover novel microbial metabolites with cell-type-selective effector properties in untargeted metabolomic inventories. Metabolites display diverse effector ... Read more >>

Nat Commun (Nature communications)
[2018, 9(1):39]

Cited: 5 times

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A Formal Approach to Xylosmin and Flacourtosides E and F: Chemoenzymatic Total Synthesis of the Hydroxylated Cyclohexenone Carboxylic Acid Moiety of Xylosmin.

Mukund Ghavre, Jordan Froese, Brennan Murphy, Razvan Simionescu, Tomas Hudlicky,

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 eutrophus B9, and Henbest epoxidation. Early attempts led to the synthesis of a C6 ... Read more >>

Org Lett (Organic letters)
[2017, 19(5):1156-1159]

Cited: 2 times

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Chemoenzymatic Synthesis of Pleiogenone A: An Antiproliferative Trihydroxyalkylcyclohexenone Isolated from Pleiogynium timorense.

Jordan Froese, Cameron Overbeeke, Tomas Hudlicky,

The first total synthesis of polyhydroxylated cyclohexenone 1, isolated from Pleiogynium timorense and named pleiogenone A, is reported that also serves as a proof of structure and absolute configuration. Enzymatic dihydroxylation of benzoic acid with R. eutrophus B9 provided enantiomerically pure diene diol 6. Elaboration of the carboxylate moiety to ... Read more >>

Chemistry (Chemistry (Weinheim an der Bergstrasse, Germany))
[2016, 22(18):6180-6184]

Cited: 3 times

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Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives.

Mukund Ghavre, Jordan Froese, Milan Pour, Tomas Hudlicky,

This update covers the syntheses of Amaryllidaceae alkaloids since the publication of the last major review in 2008. A short summary of past syntheses and their step count is provided for the major constituents; pancratistatin, 7-deoxypancratistatin, narciclasine, lycoricidine, lycorine, and for other natural constituents, as well as for unnatural derivatives. ... Read more >>

Angew. Chem. Int. Ed. Engl. (Angewandte Chemie (International ed. in English))
[2016, 55(19):5642-5691]

Cited: 15 times

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Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast.

Yang Qu, Michael L A E Easson, Jordan Froese, Razvan Simionescu, Tomas Hudlicky, Vincenzo De Luca,

Antitumor substances related to vinblastine and vincristine are exclusively found in the Catharanthus roseus (Madagascar periwinkle), a member of the Apocynaceae plant family, and continue to be extensively used in cancer chemotherapy. Although in high demand, these valuable compounds only accumulate in trace amounts in C. roseus leaves. Vinblastine and ... Read more >>

Proc Natl Acad Sci U S A (Proceedings of the National Academy of Sciences of the United States of America)
[2015, 112(19):6224-6229]

Cited: 50 times

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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.

Jordan Froese, Jason Reed Hudlicky, Tomas Hudlicky,

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 ... Read more >>

Org Biomol Chem (Organic & biomolecular chemistry)
[2014, 12(39):7810-7819]

Cited: 1 time

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