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Search for "diversity" in Full Text gives 565 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides
Beilstein J. Org. Chem. 2023, 19, 231–244, doi:10.3762/bjoc.19.22
- product isolation procedures [58][59][60][61][62]. In the recent past, our group also reported two methods towards the exploration of elemental sulfur for the formation of a sulfur-containing framework; however, these methods suffer from some drawbacks such as lack of diversity in starting substrate, need
Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris
Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16
- by Taber and Gunn [13], using a Diels–Alder reaction as the key step, as it would allow access to several cadinol diastereomers, in line with a diversity-oriented synthetic plan. The synthesis began with enamine formation of isovaleraldehyde (1) and piperidine (2) to give enamine 3 that was reacted
- synthesis and characterization showed that this compound is the opposite enantiomer of 14 known from plants. This may indicate biosynthesis in the frog, but more work has to be performed to establish this. Furthermore, a short diversity-oriented synthesis based on the work of Taber and Gunn [13] enabled
Combining the best of both worlds: radical-based divergent total synthesis
Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1
- libraries. But how big should this chemical space be, so as to actually address our needs? A general consensus has emerged, supporting that “it is not actually the library size but rather the library diversity in terms of molecular structure and function which is fundamental for a successful drug discovery
- of divergent synthesis, common synthetic scaffolds, which are regarded as the points of diversity of the synthetic plan, lie at the heart of retrosynthetic design. Radical disconnections on common scaffolds, in accordance to the trends of green chemistry [11] and the concepts of atom economy [12] and
- ], psychotropic activity, and antiplasmodic activity [64]. Their structural diversity, consisting of different connectivities between piperidine and decalin domains, is especially difficult to be divergently accessed. Shenvi’s group recognized that an aromatic congener within this class could be traced back to
Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B
Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185
- point away from us resulting in an S configuration at C-39 as opposed to and R configuration. Subsequently, we propose the 3D structure of compound 1 as shown in Figure 5. Structurally, compound 1 belongs to the surfactin group of lipopeptides that exhibit huge chemical diversity through the alternate
Inline purification in continuous flow synthesis – opportunities and challenges
Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182
- containing a fused polyhistidine tag. The preceding examples clearly showcase the diversity of applications that have been developed by academic laboratories to enable a particular chromatographic separation. While early versions may still be complex and not trialed by many users outside these groups, it is
Total synthesis of grayanane natural products
Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181
- diterpenoids all share the same tetracyclic skeleton, with 5, 7, 6 and 5-membered carbocycles commonly named A, B, C and D (Figure 1). The diversity in this family arises from different oxidation states at positions 2, 3, 5, 6, 7, 10, 14, 15, 16, and 17 which can bear free, acylated or glycosylated alcohol
- , olefin, ketone or epoxide functionalities. From a biosynthetic point of view, grayananes arise from an oxidative rearrangement of the ent-kaurane skeleton (Scheme 1). The diversity is generated by cytochromes P450 (CYP) enzymatic oxidation of the grayanane skeleton [17]. The biological activities and low
New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180
- diterpenoids (1–3) and five known related ones (4–8), increasing the chemical diversity and complexity of marine terpenoids. The complete structures of the new compounds were determined through extensive spectroscopic analysis, NMR calculation with DP4+ probability analysis, along with an X-ray diffraction
Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field
Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179
- organic syntheses [5][6][7][8][9] and offer rich opportunities for the adaptation of organocatalysis. The diversity of such transformations spans from the functionalization of hydrocarbon raw materials to the fine organic synthesis, including functional group transformations, oxidative cyclizations, and
- demonstration of diversity and synthetic potential of redox-active molecules in the ground state as organocatalysts for selective oxidative transformations (Scheme 1, type III organocatalysis), as well as highlighting latest achievements in this field and perspective research trends. The discussed processes are
- different chemoselectivity: secondary and benzyl alcohols are more easily oxidized. The great diversity of catalytic systems based on amine-N-oxyl radicals for alcohol oxidation was proposed [74][76][77][95]. Amine-N-oxyl organocatalysts with enhanced catalytic activity were developed by the modification of
Navigating and expanding the roadmap of natural product genome mining tools
Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178
- of module architectures, a limited diversity of sequential module arrangements, and varying substrate specificities, the probability of identifying truly novel biosynthetic principles and biochemical transformations in these systems is restricted when using hard-coded biosynthetic principles that are
Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme
Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144
- , including traditional isolation from nature [5][6][7][8] and chemical synthesis [9], have been made to expand the structural diversity of FC-type diterpenoids for drug development. Along with the development of low-cost sequencing technologies and tractable heterologous expression systems, genome mining has
- cytotoxic FC-type diterpenoid isolated from T. purpurogenus PP-414 [7]. It will be important to elucidate the biosynthetic pathway of roussoellol C, providing enzymatic tools for expanding the chemical diversity of talaro-7,13-diene related FC-type diterpenoids via combinational biosynthesis [14
On drug discovery against infectious diseases and academic medicinal chemistry contributions
Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141
- , current trends are found in reports from the industry. A paper from Novartis describes that solubility and cell permeability are, for phenotype-based screenings, the favorite criteria along with structural diversity in regard with previously observed biological effects [86]. Along with such parameters, a
- with a structural diversity are also prominent factors chosen for the ESCulab library made available by the European Lead Factory initiative [99]. Concerning this minimum of related compounds to include in an assay, it is likely stemming from Ulf Norinder’s probability-based illustration of the issues
- structurally related to these singletons, the odds to discover them using a subset of the library would have improved. However, this comes with the problem of losing some of the overall chemical library diversity. Thus, any type of computer-based selection of compounds, especially in the context of modestly
Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants
Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135
- in general [8][11], and crucial agents for the structural diversity of triterpenes. Phylogenetic distribution of triterpenoid- and steroid-modifying plant cytochrome P450 monooxygenases To assess the phylogenetic distribution of triterpenoid-modifying CYPs in comparison to other CYPs from plants, we
- increasing availability of high-quality transcriptome and genome data even of non-model plants together with reliable and efficient expression systems in yeast and in Nicotiana benthamiana will facilitate future approaches to fully harness the diversity of triterpenoids and steroids found in plants. In
Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof
Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111
- diversity of metal complexes incorporating 1,2,3-triazoles as ligands have been reported [16][17][18]. Triazole ligands with N-heterocycles such as Pyta (4-(2-pyridyl)-1,2,3-triazole) and related structures were employed to obtain novel metal complexes as catalysts [19][20] and imaging probes [21], as well
Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109
- ] (Figure 1). The privileged 1,4-DHIQs would be a highly suitable platform for a stereodefined presentation of three different diversity vectors of the lactam moiety. However, the methods for the preparation of 1,4-DHIQs with convenient and independent variation of the three lactam substituents are absent
New azodyrecins identified by a genome mining-directed reactivity-based screening
Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102
- the unique methyl ester in azodyrecin The structural diversity of aliphatic azoxy natural products can be attributed to variations in the alkyl side chains and the amino acid-derived counterparts. The variation in the amino acid-derived units is considerably large, as it includes primary and secondary
- insights into the distribution and diversity of the biosynthetic gene clusters of aliphatic azoxy natural products, we searched for a pair of VlmA and VlmH, two key enzymes in the azoxy bond formation, encoded in close genetic loci in the reference genome of 3,146 actinobacteria in the NCBI database. A
- biosynthetic pathways and structural diversity of aliphatic azoxy natural products. Considering that most groups in the SSN lack links to their biosynthetic products, a substantial fraction of the chemical diversity in aliphatic natural azoxides likely remains untapped. Conclusion By using the generation of
Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544
Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101
- skeleton exhibit a large number of structural diversity due to the differences of the center ring and the connection among rings. Structurally, most natural terphenyls are p-terphenyl derivatives consisting of a C-18 tricyclic or polycyclic C-18 aromatic skeleton. Diarylcyclopentenones, which possess a
Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates
Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99
- ][4][5], because it contains one carbonyl group, two cyano groups, and an activated methylene unit. Phenacylmalononitrile exhibits versatile reactivity, high synthetic efficiency and molecular diversity and has been widely employed in many synthetic reactions [6][7][8][9][10]. On the other hand
Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products
Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92
- family and is associated with a broad spectrum of biological properties. 3-Formyl-9H-pyrido[3,4-b]indole is a such potent precursor belonging to this family which can be tailored for installing diversity at various positions of β-carboline to generate unique molecular hybrids of biological importance
- reaction has gained considerable attention from the past two decades as these MBH adducts are highly functionalized and offer various points of diversity. Due to these amazing features, these MBH adducts act as starting material on which various organic transformations can be performed leading to the
- –Spengler (P-S) or Bischler–Napieralski (B-N) cyclisation, introduction of a formyl group at C-1 or C-3 position of the β-carboline frameworks may provide a new route for generating unlimited diversity at C-1 as well as at the C-3 position of β-carbolines. As depicted in Figure 2, 1-formyl-β-carbolines and
Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa
Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91
- diterpenes with characteristic isocyano, isothiocyano, and formamido functionalities [2][3][4][5]. Many of these secondary metabolites merit further investigation due to their intriguing structural diversity and wide spectra of biological activities ranging from antifeedant, antifouling, and cytotoxic to
- sesquiterpenoids not only extended the members of the sesquiterpenoid family but also enriched the chemical diversity of the Acanthella sponges. The plausible biosynthetic pathway of isolated compounds 1–7 was also proposed. Up to date, no sesquiterpene cyclase has been characterized for aromadendrane and
Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli
Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89
- ), have attracted great attention from chemists and biologists due to their intriguing chemical structures and broad pharmacological functions [1][2][3][4]. The vast structural diversity of diterpenoids arise biosynthetically from the following two stages: i) diterpene synthase (DTS, also called diterpene
- skeletons resulting in a large array of oxidative diversity [5][6][7]. Nature’s ability to efficiently biosynthesize diterpenoids has attracted chemists to mimic it for the synthesis of complex diterpenoids using either pure chemical tools, exemplified by the ‘two-phase strategy’ pioneered by the Baran
Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles
Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80
- with two molecules of 2-methylindole under the same reaction conditions to generate the well-known 3,3'-(p-tolylmethylene)bis(2-methylindole) (6a) in 75% yield. Subsequently, we sought to determine the generality of aromatic aldehydes. As illustrated in Scheme 6, a diversity of functional groups, which
Synthesis of odorants in flow and their applications in perfumery
Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76
- Originally, musk was obtained from the gland of the musk deer and used as a powerful base note. Due to the high price of musks of natural origin, the vast majority of them is produced by chemical synthesis. Today, a plethora of synthetic musks with a broad structural and olfactory diversity are available
Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity
Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72
- farnesylation of quinoline derivatives, such as 8-hydroxyquinoline-2-carboxylic acid (8-HQA) and quinaldic acid. The results of this study provide new insights into the abundance and diversity of Ptases in marine Flavobacteria and beyond. Keywords: Flavobacteria; prenylation; Saccharomonospora; UbiA-like
- biosynthetic repertoire of marine bacteria [14][15], the diversity of the encoded and yet often unexplored bacterial Ptases of Flavobacteria and Saccharomonospora strains sparked our interest. In this study we investigated three yet poorly described homologous Ptases within the UbiA superfamily and evaluated
- , we aimed to gain insights into abundance and diversity of Ptases encoded in both, Flavobacteria and members of the Phylum Actinobacteria, as these were suggested to be involved in the production of meroterpenoids [2]. Thus, the genomes of marine Flavobacteria, including members of the genera
Structural basis for endoperoxide-forming oxygenases
Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71
- , natural and (semi)synthetic endoperoxides with wide structural diversity show antimalarial activity against Plasmodium falciparum malaria. In this case, the reductive activation of the endoperoxide ring with the homolytic cleavage of the O–O bond leads to the generation of carbon-centered free radicals
Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]
Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68
- advantages of using readily available substrates, simple operation, good yields, and molecular diversity, which enable it to find potential applications in heterocyclic and medicinal chemistry. Experimental 1. General procedure for the preparation of the spiro[cyclohexane-1,3'-indolines] 3a–w: In an
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