Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)

• Cora Hertzer,
• Stefan Kehraus,
• Nils Böhringer,
• Fontje Kaligis,
• Robert Bara,
• Dirk Erpenbeck,
• Gert Wörheide,
• Till F. Schäberle,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132

• Ackers et al. in 2007 [86], see also Erpenbeck et al. from 2020 [87] (Supporting Information File 1). Specimens were stored in ethanol (96%) at −20 °C until further extraction and processing in the laboratories at the University of Bonn. A part of the collected sea slug and substrate materials will be

• finally stored at the Sam Ratulangi University, Manado, Indonesia, in the Reference Collection under the numbers SRU2015/01 and SRU2016/02. A fraction of the sponge material is stored in the Bavarian State Collection for Paleontology and Geology under collection number SNSB-BSPG.GW41291. Extraction and

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• often toxic solvents. The presence of these solvents affected the whole synthesis as the final material required rigorous purification extraction procedures with excess of water or volatile solvents to remove residual solvent inside the material’s structure. The removal of any synthetic contamination is

• ζ-potential detected. The elemental analyses showed the presence of nitrogen even after pressurized solvent extraction (PSE) and this was attributed to the presence of reactive imidazolyl carbonyl groups (IM). In an ideal reaction, the carbonyl diimidazole should react completely with two hydroxy

• the organic dye, a covalent bond formation with the still reactive NS was achieved. As shown by elemental analysis, after PS extraction, the amount of nitrogen and therefore of reactive IM was very low. The experiment was conducted on nanosponges having 1:2, 1:4, 1:8 βCD/CDI ratios, and good results

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• still trapped in the resins after the extraction, which led to a dramatic loss in photosensitisation efficiency over multiple recycles as it was progressively washed out. The flow-purified resins displayed no loss of efficiency over the recycles, indicating the flow purification had effectively removed

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• mixture, which was then extracted with EtOAc. After removing the solvent, the residue was purified on a silica gel thin-layer plate (Kieselgel 60F254; Merck Co.) developed by a mixture of CHCl3/MeOH 1:1. Extraction of the collected fraction with MeOH and evaporation gave (R)-PGME amide 5a (0.6 mg): 1H NMR

Aryl-substituted acridanes as hosts for TADF-based OLEDs

• Naveen Masimukku,
• Dalius Gudeika,
• Oleksandr Bezvikonnyi,
• Ihor Syvorotka,
• Rasa Keruckiene,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

• extraction by linearly increasing voltage (CELIV) [31][32]. TOF photocurrent transients with well-visible transit times were recorded for holes in layers of compound 4 (Figure 5a). Using the values of transit times, hole-drift mobilities at different electric fields were calculated and plotted in Figure 5

• studied compounds were performed by two methods, i.e., time-of-flight (TOF) and charge extraction by linearly increasing voltage (CELIV) in the photo regime [38]. OLEDs were fabricated by vacuum deposition of inorganic and organic layers onto cleaned ITO-coated glass, applying vacuum of 10−6 Torr. The

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

• Marcin Kaźmierczak and
• Henryk Koroniak

Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69

• -dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCl) [41] significantly increased the reaction yield (86%). What is more, the reaction byproduct is water-soluble and easy to remove by extraction. Nevertheless, HOBt was still used as an additive. This reagent has recently been reported to exhibit explosive

Direct borylation of terrylene and quaterrylene

• Haruka Kano,
• Keiji Uehara,
• Kyohei Matsuo,
• Hironobu Hayashi,
• Hiroko Yamada and
• Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

• Discussion According to the literature [8], terrylene was prepared from a 3-(1-naphthyl)perylene by using 8 equivalents of AlCl3 in chlorobenzene at 80 °C for 4 h. The crude product was purified by Soxhlet extraction followed by recrystallization from toluene. After these simple manipulations, the pure

• ]. However, the crude product was not completely purified by Soxhlet extraction and by crystallization in our hands. The borylation reaction of hardly soluble crude quaterrylene gave a deep green suspension. MALDI mass spectrometry of the reaction mixture detected an ion peak at m/z = 1004.5018 (calcd for

Opening up connectivity between documents, structures and bioactivity

• Christopher Southan

Beilstein J. Org. Chem. 2020, 16, 596–606, doi:10.3762/bjoc.16.54

• . Although their expert-curated numbers are lower (i.e., ≈2 million compounds against ≈3700 human proteins), these open sources have the great advantage of being merged within PubChem. Parallel efforts have focused on the extraction of document-to-compound (D-C-only) connectivity. In the absence of molecular

• chemistry publishers. In addition, both the European and US PubMed Central portals now add chemistry look-ups from abstracts and full-text papers. However, the fully automated extraction of DARCLP has not yet been achieved. This stands in contrast to the ability of biocurators to discern these relationships

• journals e) they can be text-mined and d) consequently, over 30 million structures have entered PubChem via automated extraction [3]. Non-document sources: While this article has to be restricted to documents an increasing amount of drug discovery data is beginning to surface on the web that may never be

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• 2 days at 100 °C, a solid was obtained, which was then filtered off, washed with distilled water, and dried. In the next step, the surfactant pluronic P123 was removed by the Soxhlet extraction method to produce a white solid. Then, 58 was synthesized using 57 and copper(II) acetate in methanol at

• reflux conditions for one day. The resulting powder was filtered off, washed with methanol, and dried. Finally, excess copper was removed by the Soxhlet extraction method (Scheme 9). The 1,3-dipolar reaction of organic alkynes, organic bromides (or aryldiazonium salts or epoxides), and sodium azide

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• , common extraction with dichloromethane was not applicable, hence solid–liquid extraction with diethylamine was used. Low yields were reported for the 3- and 4-pyridyl analogs due to the difficulty associated with their extraction compared to their 2-pyridyl counterparts [54][55]. Dai and co-workers [63

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

• Fei You,
• Xing He,
• Song Gao,
• Hong-Ru Li and
• Liang-Nian He

Beilstein J. Org. Chem. 2020, 16, 351–361, doi:10.3762/bjoc.16.34

• oligomerization degree was 4. The reaction has excellent selectivity and no other byproducts were detected except water. More remarkably, a simple stratifying at room temperature will cause the separation of catalyst and product, which means the additional solvent extraction or distillation separation employed in

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku,
• Nobuyasu Matsuura,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

• Chemical, Kanagawa, Japan) 1%, and natural seawater collected in Toyama Bay, Toyama, Japan. The pH value of the medium was adjusted to 7.0 before sterilization. The inoculated flasks were incubated at 30 °C for 5 days with rotational shaking using a rotary shaker at a speed of 200 rpm. Extraction and

Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

• Ken-ichi Nakashima,
• Junko Tomida,
• Takao Hirai,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

• ) under accession numbers LC424445 (ITS) and LC424442 (26S rDNA). Fermentation, extraction, and isolation The methods of fermentation and extraction of the fungus Talaromyces sp. ECN211 were performed in a similar manner as described previously [9]. The fungus Talaromyces sp. ECN211 was inoculated onto

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

• Jucleiton J. R. Freitas,
• Queila P. S. B. Freitas,
• Silvia R. C. P. Andrade,
• Juliano C. R. Freitas,
• Roberta A. Oliveira and
• Paulo H. Menezes

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

• protocol for propargylation of aldehydes based on microwave irradiation should take into account not only the reaction itself but also an effective method for the extraction of the obtained products. Despite the excellent results described on Scheme 1, a factor that must be taken into consideration is the

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• extraction Submerged fermentation was done as described by Chepkirui and co-workers [48], with minor modifications. Pure cultures were inoculated in YMG liquid medium by cutting seven mycelial plugs (1 cm × 1 cm) from an actively growing colony into a 500 mL Erlenmeyer flask containing 200 mL of the same

Two new aromatic polyketides from a sponge-derived Fusarium

• Mada Triandala Sibero,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Ocky K. Karna Radjasa,
• Agus Sabdono,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

• % yeast extract, 1.5% Pharmamedia (Traders Protein), and 1% Diaion HP-20 (Mitsubishi Chemical Co.). The inoculated flasks were placed on a rotary shaker (200 rpm) at 30 °C for 7 days. Extraction and isolation Extraction and isolation of secondary metabolites from strain KJMT.FP.4.3 were carried out in a

• , tR 12.0 min), together with 7-O-methylrhodolamprometrin (4, 7.2 mg, tR 17.4 min), O-methylSMA93 (5, 7.4 mg, tR 13.2 min), tricinonoic acid (6, 3.7 mg, tR 13.1 min), and cyclonerodiol (7, 5.4 mg, tR 11.3 min) after evaporation and extraction with EtOAc. Rhodolamprometrin (3, 4.0 mg, tR 15.2 min) was

A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones

• Daniel P. Pienaar,
• Kamogelo R. Butsi,
• Amanda L. Rousseau and
• Dean Brady

Beilstein J. Org. Chem. 2019, 15, 2930–2935, doi:10.3762/bjoc.15.287

• enriched/purer in hemiketal 5 than that obtained using THF as the solvent. Pure product was readily obtained in 70% yield after purification by column chromatography. We reasoned that the lower aqueous miscibility of 2MeTHF, as compared to THF, resulted in a more efficient product extraction procedure

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

• László Orha,
• József M. Tukacs,
• László Kollár and
• László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

• reuse of the catalyst was subsequently investigated by the model reaction of 0.5 mmol of 1a and 1.5 equiv of 2a in the presence of 0.5 mol % PdCl2(PPh3)2 at 55 °C for 2 h. After the first extraction of the product from the reaction mixture by the addition of 10 × 5 mL of pentane, 3a was isolated with a

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• the number of screens that can be done. Though genetic construction, culturing bacteria, terpenoid extraction, and chromatographic analysis can be carried out (semi-)automatedly, terpenoid structure elucidation constitutes another major bottleneck of these endeavors. At this end, the development of

Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

• Xinlu Chen,
• Tobias G. Köllner,
• Wangdan Xiong,
• Guo Wei and
• Feng Chen

Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281

• extraction temperatures. In our study, we aimed I) to determine whether P. polycephalum releases volatile terpenoids under normal growing conditions and II) to identify and characterize the genes for terpene biosynthesis in P. polycephalum. Our results will enable us to compare terpene chemistry and their

Carbazole-functionalized hyper-cross-linked polymers for CO₂ uptake based on Friedel–Crafts polymerization on 9-phenylcarbazole

• Dandan Fang,
• Xiaodong Li,
• Meishuai Zou,
• Xiaoyan Guo and
• Aijuan Zhang

Beilstein J. Org. Chem. 2019, 15, 2856–2863, doi:10.3762/bjoc.15.279

• . Then the solid product was separated by filtration, and the solid product was washed with first methanol, followed by THF, HCl/H2O 2:1 (v/v) and distilled water successively, further purified by Soxhlet extraction with MeOH for 24 h and then THF for another 24 h. Finally, the product was dried in a

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• speed ion trap, Bruker). Fungal material The fungal specimen was collected by C. Decock and J. C. Matasyoh in the Mount Elgon National Reserve [4]. The dried specimen and corresponding cultures were deposited in the MUCL collection (MUCL accession number: 56074). Extraction of the crude extract A

Unexpected one-pot formation of the 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study

• Sergey A. Dobrynin,
• Igor A. Kirilyuk,
• Yuri V. Gatilov,
• Andrey A. Kuzhelev,
• Olesya A. Krumkacheva,
• Matvey V. Fedin,
• Michael K. Bowman and
• Elena G. Bagryanskaya

Beilstein J. Org. Chem. 2019, 15, 2664–2670, doi:10.3762/bjoc.15.259

• and ammonium acetate was refluxed in benzene in a Dean–Stark apparatus. The reaction mixture underwent a strong tarring and after standard extraction with aqueous sulfuric acid, the main product 1 was isolated in a low yield (ca. 5%, see Scheme 1). In another experiment a much higher yield was

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

• Sarah L. Skraba-Joiner,
• Carter J. Holt and
• Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

• minutes. After cooling, products were isolated by careful neutralization with saturated aqueous NaHCO3 and extraction with dichloromethane. The crude product mixture was purified by flash chromatography then analyzed using 1H NMR. The presence of oligomeric material was assessed on crude isolated product

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• coverage of the grains. Extraction of the grains with acetone, followed by partitioning of the aqueous residue with EtOAc and defatting with hexane, provided an enriched extract of non-polar secondary metabolites. Fractionation by reversed-phase preparative HPLC (Figures S1 and S2 in Supporting Information

• profile. Preparative cultivation, extraction and isolation Two preparative-scale cultivations were carried out to produce sufficient quantities of the nanangenine family for characterisation and bioassay. Cultivation conditions were identical with the exception of growth medium. Culture A was prepared