A new member of the fusaricidin family – structure elucidation and synthesis of fusaricidin E

• Marcel Reimann,
• Louis P. Sandjo,
• Luis Antelo,
• Eckhard Thines,
• Isabella Siepe and
• Till Opatz

Beilstein J. Org. Chem. 2017, 13, 1430–1438, doi:10.3762/bjoc.13.140

• of the GHPD side chain building block. Thus, Cudic’s SPPS approach should be combined with the advantages of the late stage coupling employed by Jolliffe. Synthesis The C13-fragment was prepared starting from erucamide (6) in three simple operations. Reduction of the amide with lithium aluminium

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• ether cleavage. Aluminium- and borohydrides and the use of sodium hydride Reduction of α-aminonitriles Bifunctional α-aminonitriles exhibit several modes of reactivity. Recent reviews demonstrated the richness of this chemistry and emphasized synthetic applications particularly in heterocyclic chemistry

• and 22 (derived from the reaction of 23 and NaH) is efficient for this chain reaction. Stable intermediates 23 and 24 were fully characterized while the unstable complex 20 was only characterized with 1H NMR. Reduction of other substrates The reductive decyanation promoted by aluminium- and

• range of nitriles including the most challenging alkanenitriles and allow a large functional group tolerance. The decyanation of α-aminonitriles by aluminium- and borohydrides has been widely investigated and offers synthetic applications in heterocyclic chemistry. Recent developments using N

3D printed fluidics with embedded analytic functionality for automated reaction optimisation

• Andrew J. Capel,
• Andrew Wright,
• Matthew J. Harding,
• George W. Weaver,
• Yuqi Li,
• Russell A. Harris,
• Steve Edmondson,
• Ruth D. Goodridge and
• Steven D. R. Christie

Beilstein J. Org. Chem. 2017, 13, 111–119, doi:10.3762/bjoc.13.14

• -power energy source, typically a laser, to selectively melt a powder bed into a single solid body [17]. SLM can manufacture parts in a range of chemically inert and thermally stable metals such as stainless steel [18], aluminium and titanium [19][20], and is therefore an attractive technique for a

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

• Matthias C. Letzel,
• Hans J. Schäfer and
• Roland Fröhlich

Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5

• lithium aluminium hydride in THF to 3 and 31a in 90% (Scheme 5) and with 30b (Scheme 5) and DIBAL in toluene 92% of 31b were obtained [50]. 30c could be cleaved with lithium aluminium hydride in THF to 83% 3 and 90% 31c [51]. However, to our great disappointment the successful cleavage with 30c could not

• be transferred to the structurally similar compounds 23a/b and 25a/b. Using the same reaction conditions as with 30a both with lithium aluminium hydride in THF and DIBAL in toluene with 23a/b and 25a/b the starting material was completely reisolated. Apparently the carbonyl group is so much shielded

New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates

• Darren L. Riley,
• Joseph P. Michael and
• Charles B. de Koning

Beilstein J. Org. Chem. 2016, 12, 2609–2613, doi:10.3762/bjoc.12.256

• trace amounts of triphenylphosphine residues; our best yield for the product was only 25% [19]. Reduction of the diastereomeric mixture of esters 12b to the corresponding alcohols was achieved with a slurry of lithium aluminium hydride in diethyl ether. The reduction afforded a mixture of

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• obtained from commercial suppliers and were used without further purification. The NMR and UV–vis spectra were recorded on Brucker Avance 500-DRX (Bruker, Germany) and Carry 100 spectrometers (Varian, USA), respectively. TLC was performed on TLC aluminium sheets covered with silica gel 60 F254. Low

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247

• LTQ FT Ultra (Thermo Fischer Scientific, Bremen, Germany) system. TLC was carried out on TLC Silicagel 60 F254 on 20 × 20 aluminium sheets (Merck) and preparative TLC was performed using Silicagel 60 F254+366 (Merck) coated glass plates. Column chromatography was performed using Geduran Si 60 (Merck

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

• Martin Obst and
• Burkhard König

Beilstein J. Org. Chem. 2016, 12, 2358–2363, doi:10.3762/bjoc.12.229

• 4-methoxyphenyl methyl carbinol from Fluorochem. Riboflavin tetraacetate was synthesized from riboflavin (Acros Organics) according to a procedure reported in the literature [17]. Technical data of the rod mill apparatus: 4 LEDs (455 nm, 700 mA) on a square aluminium frame (inner diameter 35 mm) and

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

• David R. Chisholm,
• Garr-Layy Zhou,
• Ehmke Pohl,
• Roy Valentine and
• Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

• reaction was conducted with a variety of quinolin-2-ones bearing differing alkyl substituents in order to ascertain whether steric effects promote collapse of the intermediate aluminium complex via fragmentation/elimination, and to assess the generality of this approach. Table 2 highlights the effect of

• as supplied, and dried before use if required with appropriate drying agents or using an Innovative Technologies Inc. Solvent Purification System. Thin-layer chromatography (TLC) was conducted using Merck Millipore silica gel 60G F254 25 glassplates and/or TLC-PET foils of aluminium oxide with

• fluorescent indicator 254 nm (40 × 80 mm) with visualisation by UV lamp or appropriate staining agents. Flash column chromatography was performed using SiO2 from Sigma-Aldrich (230–400 mesh, 40–63 μm, 60 Å), or activated neutral aluminium oxide (Alumina) from Sigma-Aldrich, and monitored using TLC. NMR

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

• Josef Schachtner,
• Patrick Bayer and
• Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2016, 12, 1798–1811, doi:10.3762/bjoc.12.170

• considered that potential excitation of other reagents could trigger competitive reaction mechanisms and pathways. The LEDs were mounted on an aluminium rod which is water-cooled from the interior to prevent (over-)heating of the LEDs and the reaction (Figure 3). White light was obtained from a commercial

• , is shown in red. Red (λmax = 633 nm), blue (λmax = 448 nm), green (λmax = 520 nm) and white (λmax = 620 nm) LEDs mounted on a water cooled aluminium cooling element. Overlap of absorption spectrum of methylene blue in acetonitrile and emission spectra of reasonably overlapping light sources. Emission

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate

• Sean P. Bew,
• Glyn D. Hiatt-Gipson,
• Graham P. Mills and
• Claire E. Reeves

Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103

• –rac-48. Dissolving this in acetonitrile the reactants were protected from light by wrapping the flask in aluminium foil and one equivalent of silver nitrate was added. The reaction was stirred for 5 hours at ambient temperature after which the reaction was complete, a simple filtration removed the

• reported [49]. The potential for (E)-3-methyl-4-chlorobut-2-en-1-ol ((E)-60) to react with silver nitrate generating (E)-10 (Scheme 1) was investigated. Dissolving it in acetonitrile, the flask was wrapped in aluminium foil and one equivalent of silver nitrate added. After stirring for 16 hours at ambient

Aluminacyclopentanes in the synthesis of 3-substituted phospholanes and α,ω-bisphospholanes

• Vladimir A. D’yakonov,
• Alevtina L. Makhamatkhanova,
• Rina A. Agliullina,
• Leisan K. Dilmukhametova,
• Tat’yana V. Tyumkina and
• Usein M. Dzhemilev

Beilstein J. Org. Chem. 2016, 12, 406–412, doi:10.3762/bjoc.12.43

• efficient one-pot process for the synthesis of 3-substituted phospholanes and α,ω-bisphospholanes was developed. The method involves the replacement of aluminium in aluminacyclopentanes, prepared in situ by catalytic cycloalumination of α-olefins and α,ω-diolefins, by phosphorus atoms on treatment with

Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates

• Michael Edmunds,
• Mohammed Abdul Raheem,
• Rebecca Boutin,
• Katrina Tait and
• William Tam

Beilstein J. Org. Chem. 2016, 12, 239–244, doi:10.3762/bjoc.12.25

• % respectively (Table 1, entries 9 and 4). The Lewis acid additives gave a large range of yields (Table 1, entries 10–14). Iron and aluminium chlorides gave low yields (22%, Table 1, entry 10 and 29%, entry 11), zirconium chloride and zinc iodide gave moderate yields (47%, Table 1, entry 12 and 48%, entry 13

Effective immobilisation of a metathesis catalyst bearing an ammonium-tagged NHC ligand on various solid supports

• Krzysztof Skowerski,
• Jacek Białecki,
• Stefan J. Czarnocki,
• Karolina Żukowska and
• Karol Grela

Beilstein J. Org. Chem. 2016, 12, 5–15, doi:10.3762/bjoc.12.2

• chloride (Scheme 1). Catalyst 8 was isolated in excellent yield after simple filtration through a short pad of neutral aluminium oxide, using a mixture of EtOAc/MeOH 92:8 v/v as eluent. We realised that one of the important properties of this complex is its insolubility in toluene, a solvent of known

• aluminium oxide, cotton-viscose wool (cosmetic) and even filter paper. In each case 5 wt % of catalyst was deposited on the selected support (see Supporting Information File 1 for details). During this part of the study we also discovered that the protocol involving fast precipitation of 8 from diluted

• ease of handling and product purification. Lower efficiency was observed in the case of catalyst supported on neutral aluminium oxide (8-Al2O3) which provided product 10 in diminished yield. On the other hand, the catalyst supported on unmodified silica gel (8-SiO2) showed the fastest initiation rate

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• Nikon SMZ-10 stereoscopic microscope. The Soft Imaging system, analySIS [31] was used to process the images. For TGA a Mettler Toledo TGA/SDTA851e instrument was employed with a nitrogen gas purge (flow rate 30 cm3/min). Indium (mp 156.6 °C) and aluminium (mp 660.3 °C) were used for all calibrations

• of fusion of indium (156.6 °C) and zinc (419.5 °C). The heat flow calibration was based on the value of ΔH of fusion of indium (28.62 J/g). Samples in the form of fine powders (mass range 2–5 mg) were sealed in crimped, vented aluminium pans and were heated at 10 K/min, with a sealed, empty pan as

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

• Tatjana Huber,
• Lara Weisheit and
• Thomas Magauer

Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273

• -catalyzed and base-mediated cyclization of carbonate 71 [45]. Reductive cleavage of the sulfone using aluminium amalgam afforded a ketone, which was converted to an exocyclic double bond by treatment with Tebbe’s reagent [42]. In order to convert the methoxy acetal to the corresponding lactone, without

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

• Thibault E. Schmid,
• Sammy Drissi-Amraoui,
• Christophe Crévisy,
• Olivier Baslé and
• Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263

• combination of copper(II) naphthenate (CuNaph) and SimplePhos L16 as the catalytic system [40]. The reported methodology involved a regioselective 1,4 ACA of trimethylaluminium followed by the trapping of the aluminium enolate intermediate with (n-butoxymethyl)diethylamine. An oxidation–elimination sequence

Investigation on the reactivity of α-azidochalcones with carboxylic acids: Formation of α-amido-1,3-diketones and highly substituted 2-(trifluoromethyl)oxazoles

• Kandasamy Rajaguru,
• Arumugam Mariappan,
• Rajendran Suresh,
• Periasamy Manivannan and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2015, 11, 2021–2028, doi:10.3762/bjoc.11.219

• indicated by the following symbols: s (singlet), d (doublet), t (triplet), m (multiplet). 13C NMR spectra were routinely run with broadband decoupling. Pre coated silica gel on aluminium plates (Merck) were used for TLC analysis with a mixture of petroleum ether (60–80 °C) and ethyl acetate as the eluent

Synthesis of constrained analogues of tryptophan

• Elisabetta Rossi,
• Valentina Pirovano,
• Marco Negrato,
• Giorgio Abbiati and
• Monica Dell’Acqua

Beilstein J. Org. Chem. 2015, 11, 1997–2006, doi:10.3762/bjoc.11.216

• term of yields and selectivity were achieved [20][21]. We next turned our attention to aluminium catalysis. The use of 20 mol % of ethylaluminium dichloride in chloroform or toluene at room temperature resulted in the isolation of 3a and 3'a in 35% and 30% overall yield, respectively, in excellent

Fe(II)/Et₃N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives

• Ekaterina E. Galenko,
• Olesya A. Tomashenko,
• Alexander F. Khlebnikov,
• Mikhail S. Novikov and
• Taras L. Panikorovskii

Beilstein J. Org. Chem. 2015, 11, 1732–1740, doi:10.3762/bjoc.11.189

• performed on Agilent Technologies SuperNova diffractometer at 100 K using monochromated Cu Kα radiation. Thin-layer chromatography (TLC) was conducted on aluminium sheets with 0.2 mm silica gel (fluorescent indicator, Macherey-Nagel). The isoxazoles 7 [37][38] and imidazolium salts 9 [29] were synthesized

Robust bifunctional aluminium–salen catalysts for the preparation of cyclic carbonates from carbon dioxide and epoxides

• Yuri A. Rulev,
• Zalina Gugkaeva,
• Victor I. Maleev,
• Michael North and
• Yuri N. Belokon

Beilstein J. Org. Chem. 2015, 11, 1614–1623, doi:10.3762/bjoc.11.176

• one-component aluminium-based catalysts for the reaction between epoxides and carbon dioxide have been prepared. The catalysts are composed of aluminium–salen chloride complexes with trialkylammonium groups directly attached to the aromatic rings of the salen ligand. With terminal epoxides, the

• mixture and reused. Keywords: aluminium; carbon dioxide; cyclic carbonate; epoxide; salen; Introduction Carbon dioxide is a renewable and inexpensive carbon source, so great efforts have been directed at developing novel methods for the valorization of this abundant raw material [1]. One way of

• capability (via the anion in the case of catalysts containing ammonium salts), with a concomitant increase in their activity [12][13]. Recently, more environmentally benign aluminium-based complexes, including salen complexes, have been introduced to catalyse cyclic carbonate production [14]. The performance

Surprisingly facile CO₂ insertion into cobalt alkoxide bonds: A theoretical investigation

• Willem K. Offermans,
• Claudia Bizzarri,
• Walter Leitner and
• Thomas E. Müller

Beilstein J. Org. Chem. 2015, 11, 1340–1351, doi:10.3762/bjoc.11.144

• explored in several studies. Rieger et al. studied the mechanisms of the copolymerisation by homogeneous chromium(III)– and aluminium(III)–salen complexes and by heterogeneous zinc-dicarboxylates [30][31]. Experimental work on the chromium(III)– and aluminium(III)–salen complexes was combined with a

• , the insertion step into an Al(III)-alkoxide bond is a simple intramolecular process with a small activation energy (∆E# = 9.12 kcal/mol) [30][51]. Nevertheless, a bimetallic aluminium complex is considered in the mechanism. Since it is a bimolecular reaction, the Gibbs energies will be higher. Carbon

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

• /Micromass) device with a resolution of 5000 RP at 5%. Thin-layer chromatography (TLC) was carried out on aluminium sheets precoated with silica gel 60 F254. Microwave irradiations were realized using an Anton Paar Monowave 300 apparatus. Microwave heating was performed with a single mode cavity Discover

Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki–Heck cross-coupling reaction

• Jerzy Zakrzewski and
• Bogumiła Huras

Beilstein J. Org. Chem. 2015, 11, 1155–1162, doi:10.3762/bjoc.11.130

• were obtained as red solids. TLC was performed on silica gel Merck aluminium roll 5562 or aluminium sheets 5554. Column chromatography was performed using Merck 1.09385.1000 or Zeochem 60 hyd 40–63 μm silica gel (0.040–0.063 mm, 230–400 mesh), respectively. TLC visualisation: UV 254 nm light and/or

Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams

• Katherine M. Byrd

Beilstein J. Org. Chem. 2015, 11, 530–562, doi:10.3762/bjoc.11.60

• copper in CA reactions will preferentially form the 1,4-addition product [1]. Since then, copper has been the most commonly used metal in DCA and ECA reactions. In terms of the nucleophiles that are used, mainly alkyl organometallic reagents derived from zinc, aluminium, lithium and magnesium are used [1