Georgios Vassilikogiannakis - Academia.edu (original) (raw)
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Papers by Georgios Vassilikogiannakis
![Research paper thumbnail of A mechanistic comparison between [2+2] and [4+2] cycloadditions of tetracyanoethylene to 2,7-dimethyl-2,trans-4,6-octatriene. A very remote secondary H/D isotope effect](https://attachments.academia-assets.com/53256015/thumbnails/1.jpg)
](Tetrahedron Letters, 1998
Angewandte Chemie International Edition, 2017
A highly efficient and general singlet-oxygen-initiated one-pot transformation of readily accessi... more A highly efficient and general singlet-oxygen-initiated one-pot transformation of readily accessible furans into octahydroindole scaffolds has been developed.
The Journal of Organic Chemistry, 2016
Photooxygenation of 2-thiophenyl-substituted furans in ethanol leads to the rapid, regiocontrolle... more Photooxygenation of 2-thiophenyl-substituted furans in ethanol leads to the rapid, regiocontrolled, and quantitative synthesis of γ-hydroxybutenolides. The carbonyl group in butenolide holds the position of thiophenyl moiety in reacting furans. Decomposition of the initially formed [4 + 2] endoperoxide into products through a radical chain mechanism is proposed, as the fate of thiophenyl moiety is its transformation into ethyl phenylsulfenate (PhS-OEt) and diphenyldisulfide. Under the reaction conditions, the sulfenate is fast oxidized into the corresponding sulfinate.
Organic Letters, 2016
(+)-Yaoshanenolide B was synthesized employing as a key step an endo- and face-selective Diels-Al... more (+)-Yaoshanenolide B was synthesized employing as a key step an endo- and face-selective Diels-Alder reaction between natural R-(-)-α-phellandrene and the exocyclic double bond of a 5-methylene-2(5H)-furanone. The dienophile furanone was prepared by photooxygenation of a suitably substituted 2-thiophenylfuran followed by dehydration of the resulting γ-hydroxybutenolide. Through this synthesis, the initially proposed structure for (+)-yaoshanenolide B has been revised to the 1R,2S,4R,7R,1″S diastereomer.
Org Lett, 2009
Photooxygenation of 2-(beta-hydroxyalkyl) furans affords, in one synthetic operation and in high ... more Photooxygenation of 2-(beta-hydroxyalkyl) furans affords, in one synthetic operation and in high yields, 3-keto-tetrhydrofuran motifs via intramolecular Michael-type addition to the 1,4-enedione intermediate.
Chemistry - A European Journal, 2016
A novel chemoselective ligation methodology has been developed for the facile construction of pep... more A novel chemoselective ligation methodology has been developed for the facile construction of peptide-based fluorescent probes. Furan-containing peptides were activated by singlet oxygen and covalently engaged by nitrogen nucleophiles to yield stable conjugates. Singlet oxygen was compatible with sensitive amino acid residues within the peptides and a range of fluorophores, bearing different functionalities, were successfully incorporated, illustrating the broad scope of the developed strategy.
Org Lett, 2007
A [4+2]-cycloaddition between singlet oxygen and a furan, followed by an ene reaction and ketaliz... more A [4+2]-cycloaddition between singlet oxygen and a furan, followed by an ene reaction and ketalization, in one synthetic operation, was used for the synthesis of (+)-premnalane A. The first example of a singlet oxygen ene reaction that furnishes exclusively a Z-double bond is noted.
Angewandte Chemie International Edition, 2016
A highly adaptable method targeting the ubiquitous and very important pyrrolizidine and indolizid... more A highly adaptable method targeting the ubiquitous and very important pyrrolizidine and indolizidine scaffolds is presented. The general synthetic utility of the method is underscored by its application to the rapid and easy synthesis of five natural products starting from readily accessible alkylfuran precursors. These unprotected primary furylalkylamines are subjected to photooxygenation conditions, which initiate a complex cascade reaction sequence concluding with the production of high value motifs. This sequence can be tailored to need by varying the choice of both photosensitizer and base additive.
Org Lett, 2009
... Elias Pavlakos, Thomas Georgiou, Maria Tofi, Tamsyn Montagnon and Georgios Vassilikogiannakis... more ... Elias Pavlakos, Thomas Georgiou, Maria Tofi, Tamsyn Montagnon and Georgios Vassilikogiannakis*. Department of Chemistry, University of Crete, Vasilika Vouton, 71003 Iraklion, Crete, Greece. Org. Lett. , 2009, 11 (20), pp ...
![Research paper thumbnail of Regio- and Stereoselectivity of the [2 + 2] Photocycloaddition of Acyclic Enones to C 60](https://attachments.academia-assets.com/53256008/thumbnails/1.jpg)
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Tetrahedron Letters, 1998
![Research paper thumbnail of ChemInform Abstract: Mechanism of the [2 + 2] Photocycloaddition of Fullerene C60 with Styrenes](https://attachments.academia-assets.com/53256011/thumbnails/1.jpg)
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Organic Letters, 2015
The first total synthesis of pandamarine, an alkaloid isolated from Pandanus amaryllifolius is re... more The first total synthesis of pandamarine, an alkaloid isolated from Pandanus amaryllifolius is reported. The key step of this extremely short (six steps in total) and protecting group-free synthesis is a highly efficient cascade reaction sequence initiated by the photooxidation of an easily accessible and symmetric difuran precursor.
Tetrahedron Letters, 1998
Angewandte Chemie International Edition, 2017
A highly efficient and general singlet-oxygen-initiated one-pot transformation of readily accessi... more A highly efficient and general singlet-oxygen-initiated one-pot transformation of readily accessible furans into octahydroindole scaffolds has been developed.
The Journal of Organic Chemistry, 2016
Photooxygenation of 2-thiophenyl-substituted furans in ethanol leads to the rapid, regiocontrolle... more Photooxygenation of 2-thiophenyl-substituted furans in ethanol leads to the rapid, regiocontrolled, and quantitative synthesis of γ-hydroxybutenolides. The carbonyl group in butenolide holds the position of thiophenyl moiety in reacting furans. Decomposition of the initially formed [4 + 2] endoperoxide into products through a radical chain mechanism is proposed, as the fate of thiophenyl moiety is its transformation into ethyl phenylsulfenate (PhS-OEt) and diphenyldisulfide. Under the reaction conditions, the sulfenate is fast oxidized into the corresponding sulfinate.
Organic Letters, 2016
(+)-Yaoshanenolide B was synthesized employing as a key step an endo- and face-selective Diels-Al... more (+)-Yaoshanenolide B was synthesized employing as a key step an endo- and face-selective Diels-Alder reaction between natural R-(-)-α-phellandrene and the exocyclic double bond of a 5-methylene-2(5H)-furanone. The dienophile furanone was prepared by photooxygenation of a suitably substituted 2-thiophenylfuran followed by dehydration of the resulting γ-hydroxybutenolide. Through this synthesis, the initially proposed structure for (+)-yaoshanenolide B has been revised to the 1R,2S,4R,7R,1″S diastereomer.
Org Lett, 2009
Photooxygenation of 2-(beta-hydroxyalkyl) furans affords, in one synthetic operation and in high ... more Photooxygenation of 2-(beta-hydroxyalkyl) furans affords, in one synthetic operation and in high yields, 3-keto-tetrhydrofuran motifs via intramolecular Michael-type addition to the 1,4-enedione intermediate.
Chemistry - A European Journal, 2016
A novel chemoselective ligation methodology has been developed for the facile construction of pep... more A novel chemoselective ligation methodology has been developed for the facile construction of peptide-based fluorescent probes. Furan-containing peptides were activated by singlet oxygen and covalently engaged by nitrogen nucleophiles to yield stable conjugates. Singlet oxygen was compatible with sensitive amino acid residues within the peptides and a range of fluorophores, bearing different functionalities, were successfully incorporated, illustrating the broad scope of the developed strategy.
Org Lett, 2007
A [4+2]-cycloaddition between singlet oxygen and a furan, followed by an ene reaction and ketaliz... more A [4+2]-cycloaddition between singlet oxygen and a furan, followed by an ene reaction and ketalization, in one synthetic operation, was used for the synthesis of (+)-premnalane A. The first example of a singlet oxygen ene reaction that furnishes exclusively a Z-double bond is noted.
Angewandte Chemie International Edition, 2016
A highly adaptable method targeting the ubiquitous and very important pyrrolizidine and indolizid... more A highly adaptable method targeting the ubiquitous and very important pyrrolizidine and indolizidine scaffolds is presented. The general synthetic utility of the method is underscored by its application to the rapid and easy synthesis of five natural products starting from readily accessible alkylfuran precursors. These unprotected primary furylalkylamines are subjected to photooxygenation conditions, which initiate a complex cascade reaction sequence concluding with the production of high value motifs. This sequence can be tailored to need by varying the choice of both photosensitizer and base additive.
Org Lett, 2009
... Elias Pavlakos, Thomas Georgiou, Maria Tofi, Tamsyn Montagnon and Georgios Vassilikogiannakis... more ... Elias Pavlakos, Thomas Georgiou, Maria Tofi, Tamsyn Montagnon and Georgios Vassilikogiannakis*. Department of Chemistry, University of Crete, Vasilika Vouton, 71003 Iraklion, Crete, Greece. Org. Lett. , 2009, 11 (20), pp ...
Tetrahedron Letters, 1998
Organic Letters, 2015
The first total synthesis of pandamarine, an alkaloid isolated from Pandanus amaryllifolius is re... more The first total synthesis of pandamarine, an alkaloid isolated from Pandanus amaryllifolius is reported. The key step of this extremely short (six steps in total) and protecting group-free synthesis is a highly efficient cascade reaction sequence initiated by the photooxidation of an easily accessible and symmetric difuran precursor.