Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• ) Regioselective enzymatic acylation of natural products. Natural products are traditionally classified into groups of substances (terpenes, alkaloids, amino acids, lipids, etc), depending on their biosynthetic origin and on their chemical and structural features [19][20][21]. The complex structures of most of

Why base-catalyzed isomerization of N-propargyl amides yields mostly allenamides rather than ynamides

• Armando Navarro-Vázquez

Beilstein J. Org. Chem. 2015, 11, 1441–1446, doi:10.3762/bjoc.11.156

• employing harsh reaction conditions. The outcome of the isomerization process seems to subtlety depend on the structural features of the N-propargyl compound. Similar issues have been observed for carbamates or phosphoramides [8]. In summary, the isomerization process is not yet well understood and, quoting

Spiro annulation of cage polycycles via Grignard reaction and ring-closing metathesis as key steps

• Sambasivarao Kotha,
• Mohammad Saifuddin,
• Rashid Ali and
• Gaddamedi Sreevani

Beilstein J. Org. Chem. 2015, 11, 1367–1372, doi:10.3762/bjoc.11.147

• are interesting targets because of their unusual structural features such as the deformation of the ideal C–C bond angles, high degree of symmetry and the enhanced ring strain etc. [5][6][7][8][9][10][11][12][13][14][15][16][17][18]. The structures of a variety of intricate cage systems, for example

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• and nanomaterials is a challenging task. Huang and co-workers [165] have reported a taco complex template method to synthesize a cryptand/paraquat [2]rotaxane and [2]catenane (e.g., 207) by using RCM as a key step. Structural features and interesting bioactivity of the hirsutellones have grabbed the

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

• Rym Hassani,
• Mahjoub Jabli,
• Yakdhane Kacem,
• Jérôme Marrot,
• Damien Prim and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2015, 11, 1175–1186, doi:10.3762/bjoc.11.132

• structural features have been used in diverse reactions [8]. The importance of these ligands lies in the fact that the stereogenic centers are kept in close proximity to the metal and thereby having a strong and direct influence on the stereochemical course of the metal-catalyzed process. Oxazolines possess

Donor–acceptor type co-crystals of arylthio-substituted tetrathiafulvalenes and fullerenes

• Xiaofeng Lu,
• Jibin Sun,
• Shangxi Zhang,
• Longfei Ma,
• Lei Liu,
• Hui Qi,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 1043–1051, doi:10.3762/bjoc.11.117

• co-crystals of fullerene (as the acceptor) and arylthio-substituted tetrathiafulvalene derivatives (Ar-S-TTF, as the donor) were prepared and their structural features were thoroughly investigated. The formation of co-crystals relies on the flexibility of Ar-S-TTF and the size matches between Ar-S

• factors to stabilize the resulting supramolecular structures. Meanwhile, the solid state absorption study indicates that the inclusion complexes display a photoexcited electronic transition between Ar–S–TTF and C60/C70. To gain further insight into the structural features of Ar-S-TTF upon complexation

• to the short axis of C70 (10 Å), thus C70 molecules form one-dimensional (1D) columnar arrays along this direction. The structural features for both donor–acceptor interaction mode and fullerene arrangement of 7·C60, 8·C60, and 1·C70 are very similar to that of 5·C70. Type II co-crystals Among the

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• glycochemistry and medicinal chemistry [1][2][3][4][5]. C-Glycosides, especially aryl-C-glycosides, are the main structural features of a number of biologically active natural products such as pluramycins (antibacterial and antitumor activities), angucyclines (antibacterial, antitumor activities, and inhibitors

Highly selective generation of vanillin by anodic degradation of lignin: a combined approach of electrochemistry and product isolation by adsorption

• Dominik Schmitt,
• Carolin Regenbrecht,
• Marius Hartmer,
• Florian Stecker and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 473–480, doi:10.3762/bjoc.11.53

• be an alternative for petroleum-based production of fuels as well as fine chemicals [5][6][7]. Since the middle of the last century, the large amount of aromatic structural features making up the polymer led to much effort concerning efficient degradation methods into high value fine chemicals like

Synthesis and chemosensing properties of cinnoline-containing poly(arylene ethynylene)s

• Natalia A. Danilkina,
• Petr S. Vlasov,
• Semen M. Vodianik,
• Andrey A. Kruchinin,
• Yuri G. Vlasov and
• Irina A. Balova

Beilstein J. Org. Chem. 2015, 11, 373–384, doi:10.3762/bjoc.11.43

• these complexes have been isolated [67]. Therefore, two structural features in the obtained oligomer chains can be responsible for the interaction with Pd 2+ cations: conjugated triple bonds (and/or the additional ethynyl moiety in the case of compound 10b) and a cinnoline ring. In order to determine

Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines

• Carolin Edinger,
• Jörn Kulisch and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 294–301, doi:10.3762/bjoc.11.34

• , if the size of the substituent is further increased, the electrochemical conversion is significantly impaired. Structural features of 8-substituted menthylamines 1. Synthetic strategies to menthylamines. Stereoselective synthesis of 8-substituted (1R,3R,4S)-menthylamines. Influence of the cathode

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• . 5.5–6) yielding reversible positive charge. Here are also described novel approaches to reversible positively charged (DPP and DIP derivatives [45]), which are related to remarkable structural features of the naturally occurring benzophenanthridine alkaloids – pH-dependent structural transition

• between the iminium (positively charged) and alkanolamine (neutral) form [46]. Structural features of phenanthridines and phenanthridinium cations related to DNA and RNA binding Structural studies on the phenanthridine system were mostly driven by its most widespread use as DNA and RNA intercalator

• (Figure 1) and/or fluorescent marker (ethidium bromide/propidium iodide) for ds-DNA and ds-RNA [47]. The phenanthridine structural features incorporate a unique set of properties related to the interaction with DNA and RNA (Figure 1): size and curvature of the aromatic surface corresponds to the basepair

Anomalous diffusion of Ibuprofen in cyclodextrin nanosponge hydrogels: an HRMAS NMR study

• Monica Ferro,
• Franca Castiglione,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2014, 10, 2715–2723, doi:10.3762/bjoc.10.286

• – amorphous [13], thus preventing the possibility of structural assessment via diffraction methods and making a thorough structural characterization a still open investigation field. The main structural features have been obtained, so far, by a combined use of solid state 13C CP-MAS NMR, FTIR and Raman

Regio- and stereoselective synthesis of new diaminocyclopentanols

• Evgeni A. Larin,
• Valeri S. Kochubei and
• Yuri M. Atroshchenko

Beilstein J. Org. Chem. 2014, 10, 2513–2520, doi:10.3762/bjoc.10.262

• -purin-6-amine (7d) were used as nucleophiles (Figure 1). Starting amines were selected based on the fact that these motifs are common structural features in drug molecules. Optimization of the epoxide ring opening reaction of 3a The opening of epoxides with nucleophiles in the presence of Lewis acid or

Autonomous assembly of synthetic oligonucleotides built from an expanded DNA alphabet. Total synthesis of a gene encoding kanamycin resistance

• Kristen K. Merritt,
• Kevin M. Bradley,
• Daniel Hutter,
• Mariko F. Matsuura,
• Diane J. Rowold and
• Steven A. Benner

Beilstein J. Org. Chem. 2014, 10, 2348–2360, doi:10.3762/bjoc.10.245

• –Crick interactions (e.g., wobble, major groove binding) can also compete with Watson–Crickery (Figure 1). The work reported here began with the observation that several of the structural features of DNA that intrinsically limit autonomous assembly of standard DNA fragments might be overcome by adding

De novo macrolide–glycolipid macrolactone hybrids: Synthesis, structure and antibiotic activity of carbohydrate-fused macrocycles

• Richard T. Desmond,
• Anniefer N. Magpusao,
• Chris Lorenc,
• Jeremy B. Alverson,
• Nigel Priestley and
• Mark W. Peczuh

Beilstein J. Org. Chem. 2014, 10, 2215–2221, doi:10.3762/bjoc.10.229

• characteristics (Figure 3) [26]. The main structural features for these compounds are the D-glucose ring and the macrocyclic ring. The α-D-glucosyl unit in 5 and the β-D-glucosyl unit in 6 both adopt the common 4C1 chair conformation of D-pyranosides. Further, the hydroxymethyl group of the D-glucosyl unit

Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

• Michael Ghobrial,
• Marko D. Mihovilovic and
• Michael Schnürch

Beilstein J. Org. Chem. 2014, 10, 2186–2199, doi:10.3762/bjoc.10.226

• up to date. The latter compound class can be considered as a combination of structural features of general structures I–IV which would lead to 1 (Figure 1), the target compounds of the present contribution. It was our aim to develop a facile synthetic route towards compounds 1 due to their prospect

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

• Marijana Radić Stojković,
• Marko Škugor,
• Łukasz Dudek,
• Jarosław Grolik,
• Julita Eilmes and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

• for the studied series of compounds showed that the essential structural features for the ICD recognition are a) the presence of DNA-binding appendages (adenine side chain and positively charged side chain) on both DBTAA side chains, and b) the presence of a short propyl linker, which does not support

• /AP3am) revealed molecular recognition of AT-DNA by the appearance of an ICD band pattern >300 nm. Significant ICD bands did not appear for other ds-DNA/RNA. A structure–activity relation for the studied series of compounds revealed that the essential structural features for the ICD recognition of AT-DNA

Chiral phosphines in nucleophilic organocatalysis

• Yumei Xiao,
• Zhanhu Sun,
• Hongchao Guo and
• Ohyun Kwon

Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

• acylations of alcohols. Our discussion is organized according to the structural features of the chiral phosphines, the reaction types, and the nature of the substrate. Because chiral phosphine-promoted Rauhut–Currier (RC) reactions [9][10] and MBH/aza-MBH reactions [21][22][23][24][25][26] have been

Building complex carbon skeletons with ethynyl[2.2]paracyclophanes

• Ina Dix,
• Lidija Bondarenko,
• Peter G. Jones,
• Thomas Oeser and
• Henning Hopf

Beilstein J. Org. Chem. 2014, 10, 2013–2020, doi:10.3762/bjoc.10.209

• the extra diacetylene bridges, compound 11 preserves the general structural features of [2.2]paracyclophanes, which are strained molecules. We have discussed these in detail in our previous paper [1], and summarize them here as follows: the single bonds in the bridges, C1–C2 and C9–C10, are elongated

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• myxobacteria. Besides the biochemical profile, the two families share common structural features and a common biosynthesis [138][139]. Among the five members of the jerangolid family, which may be considered as trunctated analogs of the ambruticins, jerangolid A is reported to be the most potent [133][134

Structure/affinity studies in the bicyclo-DNA series: Synthesis and properties of oligonucleotides containing bc^en-T and iso-tricyclo-T nucleosides

• Branislav Dugovic,
• Michael Wagner and
• Christian J. Leumann

Beilstein J. Org. Chem. 2014, 10, 1840–1847, doi:10.3762/bjoc.10.194

• angle γ. On the other hand, planarizing the C6’–C7’-bond, as in 8β and 11β, leads to a synclinal torsion angle γ and a consistent 2’-endo furanose conformation. In order to correlate structural features of the four monomers under discussions with thermal affinity of correspondingly modified

Triazol-substituted titanocenes by strain-driven 1,3-dipolar cycloadditions

• Andreas Gansäuer,
• Andreas Okkel,
• Lukas Schwach,
• Laura Wagner,
• Anja Selig and
• Aram Prokop

Beilstein J. Org. Chem. 2014, 10, 1630–1637, doi:10.3762/bjoc.10.169

• active complexes allows the identification of structural features essential for biological activity. Keywords: azides; click-chemistry; cycloadditions; cytotoxicity; titanocenes; Introduction Group 4 metallocenes and derivatives of Cp2TiCl2, in particular, continue to be in the focus of contemporary

• our cationic carbonyl-substituted titanocenes. Comparison of the three most active complexes also allows the identification of structural features essential for cytotoxic activity. First, a bulky substitution of the cyclopentadienyl ligand is favorable. Second, positioning of the triazol in close

• modular and large numbers of the complexes can in principle be prepared in short periods of time. Some of the triazole-substituted titanocenes display high cyctotoxic activity against BJAB cells. Comparison of the most active complexes allows the identification of structural features essential for

Magnesium bis(monoperoxyphthalate) hexahydrate as mild and efficient oxidant for the synthesis of selenones

• Andrea Temperini,
• Massimo Curini,
• Ornelio Rosati and
• Lucio Minuti

Beilstein J. Org. Chem. 2014, 10, 1267–1271, doi:10.3762/bjoc.10.127

• of phenylseleninic acid [5]. These methods suffer of several disadvantages such as harsh reaction conditions and limited structural features of the substrates; thus, potassium hydrogen persulfate [6] (Oxone) and m-chloroperoxybenzoic acid [4][7] (MCPBA) have been employed for the oxidation of

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

• constraints is that they force the molecule into a well-defined secondary structure. Such structural features are often found in biologically active peptides and proteins [8]. Mimicking the secondary structure is of high interest since these motifs are regularly located at the surface of peptide–peptide