Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• from 2.5 to 7.9 Mbp, biosynthetic gene clusters for siderophores, terpenes, and non-ribosomal peptides were identified by genome mining [39], suggesting a high capability of secondary metabolism in this genus. Further investigation is underway to disclose the actual diversity of metabolites from the

Earth-abundant 3d transition metals on the rise in catalysis

• Nikolaos Kaplaneris and
• Lutz Ackermann

Beilstein J. Org. Chem. 2022, 18, 86–88, doi:10.3762/bjoc.18.8

• the editor of this issue on Earth-abundant 3d metal catalysis, it was a wonderful experience to experience the diversity of 3d transition metal catalysis, which continues to address key challenges of sustainable modern molecular syntheses. The senior author owe a great debt of gratitude to all of the

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• , analysis of the structural diversity of the two isomers of P5 indicates that P5 cis (P5.1) is more disordered (see Supporting Information File 1, Table S3), which also correlates with a blue-shifted absorption minimum compared to P5 trans (P5.2). In the partially helical structures of aAxWt (i.e., second

• would be speculative to link this property of the P5 to its enhanced biological activity. Instead, we find a more likely reason for the greater activity of P5.2 over that of aAxWt in analysing the conformational diversity of the two peptides (see Supporting Information File 1, Table S2). In P5 trans

A photochemical C=C cleavage process: toward access to backbone N-formyl peptides

• Haopei Wang and
• Zachary T. Ball

Beilstein J. Org. Chem. 2021, 17, 2932–2938, doi:10.3762/bjoc.17.202

• then account for the isolation of the acetylated analogue 9. The photochemical pathway described here represents a formal oxidative olefin cleavage of vinylogous nitroaryl-modified amides and ethers. The pathway adds to the diversity of photochemical pathways known for 2-nitrophenyl systems, and the

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

• Chuanhua Qu,
• Run Huang,
• Yong Li,
• Tong Liu,
• Yuan Chen and
• Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

• preparation of highly valuable diarylmethyl sulfones are relatively scarce [24]. In addition, the important link between structural diversity and complexity with bioactivity represented by sulfones has led to the goal of developing strategies to as many these pivotal scaffolds as possible. Isocyanide is an

Me₃Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

• Krishna M. S. Adusumalli,
• Lakshmi N. S. Konidena,
• Hima B. Gandham,
• Krishnaiah Kumari,
• Krishna R. Valluru,
• Satya K. R. Nidasanametla,
• Venkateswara R. Battula and
• Hari K. Namballa

Beilstein J. Org. Chem. 2021, 17, 2765–2772, doi:10.3762/bjoc.17.186

• of aza-heterocycles with unparalleled structural diversity, and is considered to be associated with a huge range of applications in medicinal and materials sciences [5][6][7][8][9][10][11][12]. 1-Amino substituted isoquinoline derivatives are extensively studied owing to their therapeutic

Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

• Agnieszka Grajewska,
• Maria Chrzanowska and
• Wiktoria Adamska

Beilstein J. Org. Chem. 2021, 17, 2511–2519, doi:10.3762/bjoc.17.168

• exhibiting a huge range of structural diversity and biological activity [1][2][3]. Within this family several structural motifs can be identified, for instance, the isopavines, constrained alkaloids possessing the 1,2,3,4-tetrahydroisoquinoline skeleton incorporated into the double cyclized azabicyclo[3.2.2

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

• Tania Xavier,
• Sylvie Condon,
• Christophe Pichon,
• Erwan Le Gall and
• Marc Presset

Beilstein J. Org. Chem. 2021, 17, 2085–2094, doi:10.3762/bjoc.17.135

• describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access

• to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an

• ][38]. Despite its efficiency, this strategy remains limited regarding the nature of the alkoxy group of the ester function (generally Me or Et), as it arises from the parent malonate. In order to introduce diversity at this position, the privileged route is based on the opening of a Meldrum's acid

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• biosphere by structurally supporting plants, providing energy to animals, and regulating a variety of biological processes [1]. Their versatility and diversity result in a wide range of properties exploited for commercial purposes. Chemical modifications permit to broaden their applications even further

• ]. Nevertheless, the complexity and diversity of polysaccharides makes synthetic processes extremely laborious and time consuming. Several aspects are crucial to plan a successful polysaccharide synthesis. Properly designed starting materials and/or catalysts are required to ensure regio- and stereocontrol during

• suggested that XGs are not essential for the creation of the cellulose network [96]. The complexity and diversity of XGs hinder isolation from natural sources and complicates their description. A significant effort was put towards the development of enzymes for selective introduction of the side chains [97

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• a specific target, i.e., it gives access to a greater diversity of compounds to be explored [26]. In this work, a compilation of the enantioselective synthesis of coumarin derivatives using asymmetric organocatalysis is presented, highlighting the proposed mechanism pathways for the formation of the

Development of N-F fluorinating agents and their fluorinations: Historical perspective

• Teruo Umemoto,
• Yuhao Yang and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

• reagents, a match process which minimizes side reactions. Thus, these N-fluoropyridinium salts made possible the fluorination of a diversity of nucleophilic organic compounds with different reactivities ranging across aromatics, carbanions (Grignard reagents, enolate anions), active methylene compounds

• provision of free samples of Selectfluor after its commercialization resulted in many publications concerning its applications from a diversity of research groups and in a short time period (1992–1995): These included fluorinations of alkylbenzenes (entry 1, Scheme 36) [65], Grignard reagents (entry 2) [65

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

• –Crick base pairing at mixed sequences that do not have polypurine tracts is also possible, but requires chemical modifications to alter the binding properties of PNAs. These binding modes further illustrate the diversity of molecular recognition that can be achieved with PNAs. Taken together, the early

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• derivatives from azidophilic substrates and different azide derivatives. A short reaction time, good to high yield of products, high diversity, high selectivity, and ease of operation were some benefits of this methodology. The enolate reactivity with azides was compared to enamines. The best conditions were

• the triazole ring was achieved under optimized conditions. The reaction displayed extensive diversity and excellent functional group tolerance It should be noted once again that Cu-catalyzed triazoles were obtained in good to excellent yield by using 10% CuI and 10% Cu, which were subsequently

• at room temperature. First, several nonactivated arylalkynes containing electron-rich and electron-deficient groups as well as thiophene derivatives afforded the desired 5-arylated triazole derivatives. Then, the diversity of arylboronic acids was explored. The arylboronic acids containing some

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

• Thiago S. Silva and
• Fernando Coelho

Beilstein J. Org. Chem. 2021, 17, 1565–1590, doi:10.3762/bjoc.17.112

• reacted with electron-deficient alkenes (Giese-type addition) to form new C–C bonds in intra- and intermolecular fashions. The authors reported a great diversity of electron-deficient alkenes, including α,β-unsaturated carbonyl compounds like the usually less reactive acrylamide derivative 48c

Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.

• Birthe Sandargo,
• Leon Kaysan,
• Rémy B. Teponno,
• Christian Richter,
• Benjarong Thongbai,
• Frank Surup and
• Marc Stadler

Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97

• methodology is still not available. As of 2006, the family forms a sister taxon to the Omphalotaceae within the suborder of Marasmiineae (Agaricales) [2][3]. Among Basidiomycota, the Marasmiineae are most famous for their abundant chemical diversity. Metabolites with various bioactivities described from

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

• fruity aromas, orange and lemon zest, bergamot and freshly cut grass (i.e., 8–10). The floral note family represents the most popular family with a vast repertoire of aromas mostly derived from plant-based scents (i.e., 11 and 12). As can be seen the structural diversity, including the range of

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• N1,N5-substituted biguanides, that shows little variation in reactivity. By adapting these conditions, other reactants can be used such as nitrogen-containing heterocycles, other aminated nucleophiles, or ortho-substituted anilines, extending the scope of this reaction to a broader diversity of

Metal-free glycosylation with glycosyl fluorides in liquid SO₂

• Krista Gulbe,
• Jevgeņija Lugiņina,
• Edijs Jansons,
• Artis Kinens and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 964–976, doi:10.3762/bjoc.17.78

• glycoconjugates [1][2][3][4]. Due to the large diversity of glycosyl donors and acceptors there is no general glycosylation method developed so far. To ensure high yielding, as well as regio- and stereoselective glycosidic bond formation, a proper combination of glycosyl donor and acceptor, protecting and leaving

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• provided an easy access to the synthesis of complex bioactive molecules with multiple point diversity incorporating up to eight components in one-pot [8]. The pharmaceutical industry has witnessed a considerable surge in drug synthesis via multicomponent strategies [9][10][11], including the synthesis of

• capacity and modes to achieve the uphill task easily [19]. The contemporary organic chemistry procedure involving microwave heating has paved way for the molecular diversity that helps in reducing the time required for the drug discovery process. As multicomponent reactions and microwave reactions hold

• of MWA-MCR in the construction of fused polycycles with functional diversity for the generation of a library of pharmacologically active molecules. The construction of fused annulated rings are seldomly reported often achieved by a sequential addition approach [40]. Contributing to the same and

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

• Zhonglie Yang,
• Yutong Liu,
• Kun Cao,
• Xiaobin Zhang,
• Hezhong Jiang and
• Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

• derivatives, including electron-donating or electron-withdrawing substituent groups in the para- or meta positions at the benzene rings, giving corresponding products in moderate yield. This protocol is also suitable for the structural diversity of epoxides, providing a new activation approach for C(sp3)–H

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

• Maryna O. Mazur,
• Oleksii S. Zhelavskyi,
• Eugene M. Zviagin,
• Svitlana V. Shishkina,
• Vladimir I. Musatov,
• Maksim A. Kolosov,
• Elena H. Shvets,
• Anna Yu. Andryushchenko and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2021, 17, 678–687, doi:10.3762/bjoc.17.57

• containing an isoxazole moiety is of key interest in this study since previously our group reported [19] a successful usage of 3-aminoizoxazoles as unusual amine components in the Ugi-4CR reaction and here we continue to build molecular diversity of isoxazole-derived Ugi products and their successors

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• Discussion Synthesis of starting compounds for enzymatic hydroxylation In order to estimate the possible diversity of the substrates as starting materials for the biocatalytic transformation, cortisol (1) was converted to a hydroxylated steroid derivative 2 by reduction of the C20 carbonyl group with NaBH4

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• synthetic methods, the multicomponent Mannich-type condensation strategy shows a high efficiency, convergent feature, and product diversity. It can be expected that the convergent multicomponent condensation synthetic strategy will show wide applications in the preparation of biologically active

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

• Vladimir Kubyshkin,
• Rebecca Davis and
• Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

• diversity of complications that could hinder protein studies with fluoroprolines. On the other hand, in the presence of R-Flp, the folded and fully active PWA enzyme was isolated, clearly demonstrating the ability of this analog to abolish the ribosome stalling issues in vivo. This is in full agreement with

Hydrazides in the reaction with hydroxypyrrolines: less nucleophilicity – more diversity

• Dmitrii A. Shabalin,
• Evgeniya E. Ivanova,
• Igor A. Ushakov,
• Elena Yu. Schmidt and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2021, 17, 319–324, doi:10.3762/bjoc.17.29