Lukas Rycek

Lukas Rycek
Charles University in Prague | CUNI · Department of Organic Chemistry (PF)

Doctor of Philosophy

About

23
Publications
2,428
Reads
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200
Citations
Additional affiliations
November 2018 - present
Charles University in Prague
Position
  • PostDoc Position
November 2017 - October 2018
Zentiva
Position
  • API development chemist
June 2015 - October 2017
Brock University
Position
  • PostDoc Position

Publications

Publications (23)
Article
This review summarizes our work in the field of synthesis of natural products and their derivatives. Application of modern synthetic method is discussed in the context of the syntheses of both enantiomers of hydromorphone, (–)-tetrodotoxin (a marine toxin), and selaginpulvilins C and D (natural fluorene derivatives). Further, synthesis of notoincis...
Article
We report the first total synthesis of natural diarylbenzophenone selagibenzophenone C recently isolated from a plant species Selaginella tamariscina , traditionally used in folklore medicines. The framework of the natural compound is assembled via Suzuki‐Miyaura cross‐coupling and the addition of organometallic species. Following some ambiguities...
Article
Full-text available
Selagibenzophenone A (1) and its isomer selagibenzophenone B (2) were recently described as natural products from Selaginella genus plants with PDE4 inhibitory activity. Herein, we report the first total syntheses of both compounds. By comparing spectroscopic data of the synthetic compounds with reported data for the isolated material, we demonstra...
Article
A facile and unified approach to the main selaginpulvilin's framework was achieved by catalytic [2 + 2 + 2]-cyclotrimerization of a triyne with monosubtituted alkynes. The reaction proceeded with high "ortho" selectivity by using Wilkinson's catalyst (RhCl(PPh3)3) under ambient conditions with reasonable yields. The scope of the reaction with respe...
Article
This review provides a comprehensive coverage of the history, biology and chemistry of tetrodotoxin (TTX). It traces the history 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 biology of TTX...
Article
This review provides a comprehensive coverage of the history, biology and chemistry of tetrodotoxin (TTX). It traces the history 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 biology of TTX...
Article
Full-text available
The total syntheses of all stereoisomers of notoincisol A, a recently isolated natural product with potential anti-inflammatory activity, are reported. The asymmetric synthesis was conducted employing a lipase-mediated kinetic resolution, which enables easy access to all required chiral building blocks with the aim of establishing the absolute conf...
Article
A shorter and less costly alternative to Ichikawa’s [1,3]-transposition protocol for cyanates to isocyanates is described.
Article
Partial agonists of the transcription factor PPARγ (peroxisome proliferator-activated receptor γ) have shown potential for the treatment of metabolic and inflammatory conditions and novel activators serve as valuable tool and lead compounds. Based on the natural product magnolol (I) and recent structural information of the ligand–target interaction...
Article
A chemoenzymatic approach to tetrodotoxin is described by T. Hudlicky and co‐workers in their Communication (DOI: 10.1002/anie.201804602). Benzyl acetate was subjected to highly regio‐ and enantioselective dihydroxylation mediated by a robust recombinant organism, E. coli JM109 (pDTG601A), that overexpresses toluene dioxygenase. The resulting homoc...
Article
Die chemoenzymatische Synthese von Tetrodotoxin, die T. Hudlicky et al. in ihrer Zuschrift (DOI: 10.1002/ange.201804602) beschreiben, beinhaltet eine regio‐ und enantioselektive Dihydroxylierung von Benzylacetat durch einen rekombinanten Organismus, E. coli JM109 (pDTG601A), der eine Toluoldioxygenase überexprimiert. Der entstehende homochirale Die...
Article
Full-text available
The advanced intermediates in the syntheses of tetrodotoxin reported by Fukuyama, Alonso, and Sato were prepared. The key steps in the synthesis of the title compounds involved the toluene dioxygenase‐mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed to Fukuyama's intermediate in seven step...
Article
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 n...
Article
Full-text available
The nuclear receptors peroxisome proliferator-activated receptor γ (PPARγ) and its hetero-dimerization partner retinoid X receptor α (RXRα) are considered as drug targets in the treatment of diseases like the metabolic syndrome and diabetes mellitus type 2. Effort has been made to develop new agonists for PPARγ to obtain ligands with more favorable...
Article
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 complex...
Article
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 complex...
Article
A 2nd 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 m...
Chapter
This chapter treats the cross-coupling chemistry of electron-deficient N-heterocycles containing two nitrogen atoms. The chapter is ordered according to heterocycle, coupling method, and the role of the N-heterocycle within the coupling process. The focus lies on new developments in the field, e.g., regarding new catalytic systems, and covers liter...
Article
Full-text available
We present the synthesis of new derivatives of natural products magnolol (1) and honokiol (2) and their evaluation as allosteric ligands for modulation of GABAA receptor activity. New derivatives were prepared via metal assisted cross-coupling reactions in two consecutive steps. Compounds were tested by means of two-electrode voltage clamp electrop...
Article
Compared with the widespread use of carbonylative Pd-catalyzed cross-coupling reactions, similar reactions involving isocyanide insertion are almost virgin territory. We investigated the intramolecular imidoylative cross-coupling of N-(2-bromoaryl)amidines, leading to 4-aminoquinazolines. After thorough optimization of the reaction with respect to...

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