(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

Long oligodeoxynucleotides: chemical synthesis, isolation via catching-by-polymerization, verification via sequencing, and gene expression demonstration

• Yipeng Yin,
• Reed Arneson,
• Alexander Apostle,
• Adikari M. D. N. Eriyagama,
• Komal Chillar,
• Emma Burke,
• Martina Jahfetson,
• Yinan Yuan and
• Shiyue Fang

Beilstein J. Org. Chem. 2023, 19, 1957–1965, doi:10.3762/bjoc.19.146

• automated de novo synthesis of long ODNs would solve or alleviate many of these problems. Significant efforts have been made toward de novo synthesis of long ODNs through engineering of template-independent terminal deoxynucleotidyl transferase (TdT) [17]. While promising, this enzymatic method is unlikely

• novo synthesis, it is expected to be able to overcome many of the challenges, which include but are not limited to construction of genes with long repeats or complex secondary structures, currently faced by research projects in emerging areas such as synthetic biology and protein engineering. Workflow

• long ODN synthesis and purification, correct sequence selection, gene construction to protein synthesis has been established. Because the present long ODN synthesis method does not need PCR assembly or ligation of short ODNs and secondary structures of ODNs are prevented by protecting groups during de

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

• Bram Ryckaert,
• Ellen Demeyere,
• Frederick Degroote,
• Hilde Janssens and
• Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

• used dihydrodithiin-scaffolding is tentatively indicated on the target structures 70–81 [62][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79][80]. D’Alonzo, Palumbo, Guaranga and co-workers also developed a de novo synthesis of the unnatural enantiomer of the iminosugar drug miglustat

Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

• Kah Yean Lum,
• Jonathan M. White,
• Daniel J. G. Johnson,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2023, 19, 107–114, doi:10.3762/bjoc.19.11

• lead compounds without the need for de novo synthesis [5]. Baran et al. has developed an operationally simple, radical-based functionalisation strategy that allows direct transformation of C–H bonds to C–C bonds in a practical manner [11]. This strategy involves the utilisation of sodium and zinc

Vicinal ketoesters – key intermediates in the total synthesis of natural products

• Marc Paul Beller and
• Ulrich Koert

Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129

• with α-ketoester 81 furnished compound 82 with the last ring of the target (+)-gracilamine (83), which was accessible after two further steps. (−)-Irofulven Irofulven (87) is a highly cytotoxic, semisynthetic drug obtained from the illudin sesquiterpene family. In a de novo synthesis towards

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• and size of their cavity requires often tedious de-novo synthesis. Eventually, these drawbacks have been tackled by synthesizing discrete supramolecular hosts based on metal–ligand coordination-driven self-assembly [15][16][17][18][19][20][21][22][52]. This approach not only solved the issue with low

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

• Dominik Göbel,
• Marius Friedrich,
• Enno Lork and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2020, 16, 1683–1692, doi:10.3762/bjoc.16.139

• to higher structures. This is due to missing synthetic strategies to incorporate suitable linkable functionalities into those luminophores. Our group is highly interested in the de novo synthesis of small organic luminophores and in this regard, we recently developed efficient methods for the

Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

Diversity-oriented synthesis of 17-spirosteroids

• Benjamin Laroche,
• Thomas Bouvarel,
• Martin Louis-Sylvestre and
• Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

• relevant compounds [15][16][17]. Once a biologically relevant scaffold has been identified, the diversity-generating workflow can basically follow two complementary approaches, either by de novo synthesis sequentially incorporating the diversity [15][18][19], or by late functionalization of easily

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

• Matthias Wünsch,
• David Schröder,
• Tanja Fröhr,
• Lisa Teichmann,
• Sebastian Hedwig,
• Nils Janson,
• Clara Belu,
• Jasmin Simon,
• Shari Heidemeyer,
• Philipp Holtkamp,
• Jens Rudlof,
• Lennard Klemme,
• Alessa Hinzmann,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2017, 13, 2428–2441, doi:10.3762/bjoc.13.240

• amino acid analogues [22][23]. However, epimerization in the α-position frequently occurs under the alkaline reaction conditions of the Seyferth–Gilbert and the Corey–Fuchs reaction. In order to access propargylamines with modified side chains, we chose a de novo synthesis strategy, using Ellman’s

• -butylsulfinyl, R’ = Me, CHMe2, CH2CHMe2, cyclohexyl [17]. e,f) CuI or RuII-catalyzed [3 + 2] cycloadditions (CuAAC, RuAAC) [18][19][20][21]. e) R = Boc, R’ = Bn [19]. f) R = Boc, R’ = Me, CHMe2, CH2CHMe2, R’’ = Me, CHMe2, CH2Ph [21]. Two different approaches for the stereoselective de novo synthesis of

Synthesis of D-manno-heptulose via a cascade aldol/hemiketalization reaction

• Yan Chen,
• Xiaoman Wang,
• Junchang Wang and
• You Yang

Beilstein J. Org. Chem. 2017, 13, 795–799, doi:10.3762/bjoc.13.79

• protected ketoheptose building block is still attractive due to the versatile functionalization possibilities of the building block into various derivatives of D-manno-heptulose. A de novo synthesis has proved to be an attractive strategy to produce orthogonally protected carbohydrate building blocks from

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

• Alexander Bogdanov,
• Cora Hertzer,
• Stefan Kehraus,
• Samuel Nietzer,
• Sven Rohde,
• Peter J. Schupp,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2017, 13, 502–519, doi:10.3762/bjoc.13.50

• protection, alternative defensive strategies, such as the production of calcareous needles or acidic sulfates, and sequestration or de novo synthesis of toxic metabolites emerged within the opisthobranch taxa [2][3][4][5]. Adaptations and mimicry, which help to hide in habitats is frequent in marine

The EIMS fragmentation mechanisms of the sesquiterpenes corvol ethers A and B, epi-cubebol and isodauc-8-en-11-ol

• Patrick Rabe and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 1380–1394, doi:10.3762/bjoc.12.132

• requires a de novo synthesis for each isotopomer, or at least a partial degradation of a terpene and reconstruction with a 13C-labelled building block. Alternatively, a 13C-labelled terpene may be obtained by feeding of labelled precursors to the producing organism, but this strategy will require high

Olefin cross metathesis based de novo synthesis of a partially protected L-amicetose and a fully protected L-cinerulose derivative

• Bernd Schmidt and
• Sylvia Hauke

Beilstein J. Org. Chem. 2014, 10, 1023–1031, doi:10.3762/bjoc.10.102

• Bernd Schmidt Sylvia Hauke Institut für Chemie, Organische Synthesechemie, Universität Potsdam, Karl-Liebknecht-Straße 24–25, 14476 Potsdam-Golm, Germany 10.3762/bjoc.10.102 Abstract Cross metathesis of a lactate derived allylic alcohol and acrolein is the entry point to a de novo synthesis of 4

• -benzoate protected L-amicetose and a cinerulose derivative protected at C5 and C1. Keywords: carbohydrates; de novo synthesis; lactate; metathesis; ruthenium; Introduction Many drugs and bioactive natural products are glycoconjugates, which contain an aglycon part linked through glycosidic bonds to one

• literature precedence for the use of acroleins as CM partner is significantly smaller [38][39][40][41][42][43][44]. In this contribution we report a de novo synthesis of a protected L-amicetose, using a cross metathesis reaction of allyl alcohol 2 with acrolein, and the elaboration of the cross metathesis

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

• . Principally this pertains to those pyridine units installed from a generic commercially available building block and pyridines specifically prepared via de novo synthesis with the intent of tailoring the physical or metabolic stability of the compound. Often in the latter case the pyridine ring is an integral

• part of the pharmacophore rather than simply imparting a modicum of increased solubility or tuning a parameter such as LogP [22]. An important example of de novo synthesis of the pyridine core can be found in the syntheses of nicotinic acid (1.12, vitamin B3/niacin) and nicotinamide (1.18, constituent

• pioglitazone use related pyridine building blocks and aim to generate late stage intermediates that deliver the target compound upon de novo synthesis of the thiazolidinedione ring system. For instance phenyl ether 1.73 can be obtained via Williamson ether synthesis between mesylate 1.74 and phenol 1.75

The rapid generation of isothiocyanates in flow

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 1613–1619, doi:10.3762/bjoc.9.184

• isocyanides [30][31], guanidines [32][33] and thiosemicarbazides [34]. Due to the limited commercial availability of diversely functionalised isothiocyanates chemists normally pursue a de novo synthesis, which most commonly involves the condensation of an amine with thiophosgene or carbon disulfide [35][36

De novo synthesis of D- and L-fucosamine containing disaccharides

• Daniele Leonori and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 332–341, doi:10.3762/bjoc.9.38

• -Garner aldehydes. These differentially protected monosaccharide building blocks were utilized to prepare disaccharides present on the surface of Pseudomonas aeruginosa bacteria. Keywords: de novo synthesis; fucosamine; glycan; pseudomonas aeruginosa; vaccine; Introduction Protein functions are directly

• against this bacterium [24][25][26][27][28]. The synthesis of fucosamine building blocks has been reported in the literature, but it is highly affected by long synthetic sequences, extensive protecting group manipulations and expensive starting materials [29][30][31][32][33]. The de novo synthesis of rare

• sugars [34][35][36][37][38][39][40][41][42][43] provides an attractive alternative for rapid access to the required building blocks, but this approach has not been reported for D- or L-fucosamine [29][30][31][32][33][44][45][46]. Here, a full account of the de novo synthesis of differentially protected D

An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

• siRNA inhibition of the fucosyltransferase FUT1 and GDP-4-keto-6-deoxymannose-epimerase/reductase (FX-protein) [19]. The FX-protein is required for de novo synthesis of GDP-fucose from GDP-mannose [46], whereas FUT 1 catalyzes the α2 fucosylation of blood group H type 1 and Lewisy oligosaccharides. The