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Author Tomas Hudlicky

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Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate.

Mary Ann Endoma-Arias, Helen Dela Paz, Tomas Hudlicky,

The total synthesis of (+)-10-keto-oxycodone was attained from phenethyl acetate in a stereoselective manner. Absolute stereochemistry was established via enzymatic dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) that furnished the corresponding cis-cyclohexadienediol whose configuration corresponds to the absolute stereochemistry of the ring C of (+)-10-keto-oxycodone. Intramolecular Heck ... Read more >>

Molecules (Molecules (Basel, Switzerland))
[2019, 24(19):]

Cited: 0 times

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Tetrodotoxin: History, Biology, and Synthesis.

Mariia Makarova, Lukas Rycek, Josef Hajicek, Daler Baidilov, Tomas Hudlicky,

This review provides a comprehensive coverage of the history, biology and chemistry of tetrodotoxin (TTX). It traces the origin of this remarkable molecule all the way back to the ancient Chinese medicine records. The discovery of biological activity, isolation, and a brief overview of structure elucidation are summarized. Next, the ... Read more >>

Angew Chem Int Ed Engl (Angewandte Chemie (International ed. in English))
[2019, 58(51):18338-18387]

Cited: 1 time

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Chemoenzymatic Total Synthesis of ent-Oxycodone: Second-, Third-, and Fourth-Generation Strategies.

Mariia Makarova, Mary Ann A Endoma-Arias, Helen E Dela Paz, Razvan Simionescu, Tomas Hudlicky,

Four distinct approaches to ent-oxycodone were designed and accomplished. All rely on the same starting material, the diene diol derived from phenethyl acetate by the whole-cell fermentation with E. coli JM109 (pDTG601A), a strain that overexpresses toluene dioxygenase. The key step in the first-generation approach involves the construction of the ... Read more >>

J Am Chem Soc (Journal of the American Chemical Society)
[2019, 141(27):10883-10904]

Cited: 1 time

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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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Corrigendum: Cancer Cell Mitochondria Targeting by Pancratistatin Analogs is Dependent on Functional Complex II and III.

Dennis Ma, Christopher Pignanelli, Daniel Tarade, Tyler Gilbert, Megan Noel, Fadi Mansour, Scott Adams, Alexander Dowhayko, Kyle Stokes, Sergey Vshyvenko, Jonathan Collins, Tomas Hudlicky, James McNulty, Siyaram Pandey,

This corrects the article DOI: 10.1038/srep42957. ... Read more >>

Sci Rep (Scientific reports)
[2018, 8:46998]

Cited: 0 times

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Isolation, Synthesis, and Semisynthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De Novo Total Synthesis of 2- epi-Narciclasine.

Suresh Borra, Ringaile Lapinskaite, Christine Kempthorne, David Liscombe, James McNulty, Tomas Hudlicky,

An efficient protocol for the isolation of narciclasine from common Amaryllidaceae bulbs, separation from haemanthamine, and the occurrence of a trace alkaloid, 2- epi-narciclasine, are reported. Attempts to convert natural narciclasine to its C-2 epimer by Mitsunobu inversion or oxidation/reduction sequences were compromised by rearrangement and aromatization processes, through which ... Read more >>

J Nat Prod (Journal of natural products)
[2018, 81(6):1451-1459]

Cited: 4 times

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Rosmarinic Acid, a Rosemary Extract Polyphenol, Increases Skeletal Muscle Cell Glucose Uptake and Activates AMPK.

Filip Vlavcheski, Madina Naimi, Brennan Murphy, Tomas Hudlicky, Evangelia Tsiani,

Skeletal muscle is a major insulin-target tissue and plays an important role in glucose homeostasis. Impaired insulin action in muscles leads to insulin resistance and type 2 diabetes mellitus. 5' AMP-activated kinase (AMPK) is an energy sensor, its activation increases glucose uptake in skeletal muscle and AMPK activators have been ... Read more >>

Molecules (Molecules (Basel, Switzerland))
[2017, 22(10):]

Cited: 11 times

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Exploiting mitochondrial and oxidative vulnerabilities with a synthetic analog of pancratistatin in combination with piperlongumine for cancer therapy.

Dennis Ma, Tyler Gilbert, Christopher Pignanelli, Daniel Tarade, Megan Noel, Fadi Mansour, Manika Gupta, Sabrina Ma, Jesse Ropat, Colin Curran, Sergey Vshyvenko, Tomas Hudlicky, Siyaram Pandey,

Harsh adverse effects as a result of nonspecific targeting of chemotherapeutics currently pose obstacles in cancer therapy; thus, it would be invaluable to devise novel approaches to specifically target cancer cells. The natural compound pancratistatin (PST) has been shown to preferentially induce apoptosis in a variety of cancer cell types. ... Read more >>

FASEB J. (FASEB journal : official publication of the Federation of American Societies for Experimental Biology)
[2018, 32(1):417-430]

Cited: 3 times

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Applications of the Wittig-Still Rearrangement in Organic Synthesis.

Lukas Rycek, Tomas Hudlicky,

This Review traces the discovery of the Wittig-Still rearrangement and its applications in organic synthesis. Its relationship to Wittig rearrangements is discussed along with detailed analysis of E/Z- and diastereoselectivity. Modifications of the products arising from the Wittig-Still rearrangement are reviewed in the context of increased complexity in intermediates potentially ... Read more >>

Angew Chem Int Ed Engl (Angewandte Chemie (International ed. in English))
[2017, 56(22):6022-6066]

Cited: 1 time

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Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate.

Mary A A Endoma-Arias, Tomas Hudlicky,

The stereoselective total synthesis of unnatural (+)-galanthamine starting from phenethyl acetate is described. Chirality was introduced via microbial dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) to the corresponding cis-cyclohexadi-enediol, configuration of which provided the absolute stereochemistry of the ring C of (+)-galanthamine. Intramolecular Heck cyclization was used ... Read more >>

Chemistry (Chemistry (Weinheim an der Bergstrasse, Germany))
[2016, 22(41):14540-14543]

Cited: 4 times

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Cancer Cell Mitochondria Targeting by Pancratistatin Analogs is Dependent on Functional Complex II and III.

Dennis Ma, Christopher Pignanelli, Daniel Tarade, Tyler Gilbert, Megan Noel, Fadi Mansour, Scott Adams, Alexander Dowhayko, Kyle Stokes, Sergey Vshyvenko, Tomas Hudlicky, James McNulty, Siyaram Pandey,

Enhanced mitochondrial stability and decreased dependence on oxidative phosphorylation confer an acquired resistance to apoptosis in cancer cells, but may present opportunities for therapeutic intervention. The compound pancratistatin (PST) has been shown to selectively induce apoptosis in cancer cells. However, its low availability in nature has hindered its clinical advancement. ... Read more >>

Sci Rep (Scientific reports)
[2017, 7:42957]

Cited: 13 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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Carnosic acid as a component of rosemary extract stimulates skeletal muscle cell glucose uptake via AMPK activation.

Madina Naimi, Filip Vlavcheski, Brennan Murphy, Tomas Hudlicky, Evangelia Tsiani,

Compounds that increase the activity of the energy sensor AMP-activated kinase (AMPK) have the potential to regulate blood glucose levels. Although rosemary extract (RE) has been reported to activate AMPK and reduce blood glucose levels in vivo, the chemical components responsible for these effects are not known. In the present ... Read more >>

Clin Exp Pharmacol Physiol (Clinical and experimental pharmacology & physiology)
[2017, 44(1):94-102]

Cited: 6 times

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Chemoenzymatic Total Synthesis of Hydromorphone by an Oxidative Dearomatization/Intramolecular [4 + 2] Cycloaddition Sequence: A Second-Generation Approach.

Lukas Rycek, John J Hayward, Marwa Abdel Latif, James Tanko, Razvan Simionescu, Tomas Hudlicky,

A second-generation approach to the synthesis of hydromorphone by oxidative dearomatization/Diels-Alder cycloaddition was investigated. Detailed analysis of the stereochemical outcome of the [4 + 2] cycloaddition was performed first on a truncated model system as well as on the material leading to ent-hydromorphone. The stereochemical assignments were made by NMR ... Read more >>

J Org Chem (The Journal of organic chemistry)
[2016, 81(22):10930-10941]

Cited: 3 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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The quest for a practical synthesis of morphine alkaloids and their derivatives by chemoenzymatic methods.

Josephine W Reed, Tomas Hudlicky,

We became interested in approaches to morphine in the early 1990s following our immersion into the new program on the enzymatic dihydroxylation of aromatics. Larry Kwart, a former classmate of one of us at Rice University, who worked with our group at Virginia Tech in the mid-1980s, introduced to us ... Read more >>

Acc Chem Res (Accounts of chemical research)
[2015, 48(3):674-687]

Cited: 14 times

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Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide.

Sergey Vshyvenko, Mary Rose Reisenauer, Snezna Rogelj, Tomas Hudlicky,

Several unnatural derivatives of narciclasine were prepared in which the C-7 carbon was replaced with nitrogen. The 7-aza derivative and its N-oxide were prepared by the coupling of iodopicolinic acid with a conduramine unit derived chemoenzymatically from bromobenzene. Intramolecular Heck reaction was used to construct the isocarbostyryl ring system. The ... Read more >>

Bioorg Med Chem Lett (Bioorganic & medicinal chemistry letters)
[2014, 24(17):4236-4238]

Cited: 3 times

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Short chemoenzymatic total synthesis of ent-hydromorphone: an oxidative dearomatization/intramolecular [4+2] cycloaddition/amination sequence.

Vimal Varghese, Tomas Hudlicky,

A short synthesis of ent-hydromorphone has been achieved in twelve steps from β-bromoethylbenzene. The key transformations involved the enzymatic dihydroxylation of the arene to the corresponding cis-dihydrodiol, Mitsunobu coupling with the ring A fragment, oxidative dearomatization of the C3 phenol, and the subsequent [4+2] cycloaddition to form ring B of the ... Read more >>

Angew Chem Int Ed Engl (Angewandte Chemie (International ed. in English))
[2014, 53(17):4355-4358]

Cited: 10 times

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Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue.

Dana K Winter, Mary Ann Endoma-Arias, Tomas Hudlicky, John A Beutler, John A Porco,

The total synthesis of kibdelone A has been accomplished via In(III)-catalyzed arylation of a heterocyclic quinone monoketal and iodine-mediated oxidative photochemical electrocyclization for construction of the ABCD ring moiety. Enzymatic dihydroxylation of methyl 2-halobenzoate substrates was employed for synthesis of activated 2-halo-cyclohexene F-ring fragments. A one pot oxa-Michael/Friedel-Crafts process allowed ... Read more >>

J Org Chem (The Journal of organic chemistry)
[2013, 78(15):7617-7626]

Cited: 8 times

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Heteroatom analogues of hydrocodone: synthesis and biological activity.

Robert D Giacometti, Jan Duchek, Lukas Werner, Afeef S Husni, Christopher R McCurdy, Stephen J Cutler, D Phillip Cox, Tomas Hudlicky,

Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of ... Read more >>

J Org Chem (The Journal of organic chemistry)
[2013, 78(7):2914-2925]

Cited: 2 times

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Selective cytotoxicity against human osteosarcoma cells by a novel synthetic C-1 analogue of 7-deoxypancratistatin is potentiated by curcumin.

Dennis Ma, Phillip Tremblay, Kevinjeet Mahngar, Jonathan Collins, Tomas Hudlicky, Siyaram Pandey,

The natural compound pancratistatin (PST) is a non-genotoxic inducer of apoptosis in a variety of cancers. It exhibits cancer selectivity as non-cancerous cells are markedly less sensitive to PST. Nonetheless, PST is not readily synthesized and is present in very low quantities in its natural source to be applied clinically. ... Read more >>

PLoS One (PloS one)
[2011, 6(12):e28780]

Cited: 14 times

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Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.

Sergey Vshyvenko, Jon Scattolon, Tomas Hudlicky, Anntherese E Romero, Alexander Kornienko, Dennis Ma, Ian Tuffley, Siyaram Pandey,

Several C-1 homologues of pancratistatin and 7-deoxypancratistatin were synthesized by a phenanthrene-phenathridone oxidative recyclization strategy. The key steps involved the enzymatic dihydroxylation of bromobenzene, addition of an aryl alane to an epoxyaziridine, an intramolecular aziridine opening on silica gel in solid phase, and the above-mentioned recylization strategy. Experimental and spectral ... Read more >>

Can J Chem (Canadian journal of chemistry)
[2012, 90(11):932-943]

Cited: 7 times

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