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Search for "late stage modification" in Full Text gives 11 result(s) in Beilstein Journal of Organic Chemistry.
Innovative synthesis of drug-like molecules using tetrazole as core building blocks
Beilstein J. Org. Chem. 2024, 20, 950–958, doi:10.3762/bjoc.20.85
- moiety is introduced in a late-stage-modification approach, mostly from nitriles or isocyanides (Figure 1b) [13]. On the other hand, accessing diverse tetrazole scaffolds from MCRs, typically involves first de novo construction of the tetrazole scaffold and subsequent post-modifications (Figure 1c) [14
Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus
Beilstein J. Org. Chem. 2024, 20, 815–822, doi:10.3762/bjoc.20.73
- derivatives 7–9. This study marks the first discovery of natural DMTs from bacteria and unveils the role of CavA in a novel late-stage modification pathway, expanding DMT biosynthesis beyond fungi and plants. Results and Discussion Discovery of three DMTs in S. clavuligerus S. clavuligerus is notably
Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines
Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59
- , amoxapine, an ibrutinib derivative, N-desmethyl sildenafil, silodosin, and lapatinib (4d–k, 35–67%). The late-stage modification of these drug agents and their derivatives in this MCR underlined the synthetic value and high functional group tolerance (e.g., aromatic amine, amide, alcohol, heterocycle). We
Synthesis and late stage modifications of Cyl derivatives
Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19
- , such as histone deacetylases. Keywords: chelated enolate; Claisen rearrangement; HDAC inhibitor; peptide; late stage modification; Introduction Among natural products, peptidic structures have entered the limelight due to their extraordinary biological activities [1]. Often found as secondary
On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets
Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126
- , operating under mild conditions without the need of directing groups, using traceless electrons as sole redox reagents, presenting high scope and chemoselectivity. The robustness of the reaction was proved by the late-stage modification of pharmaceutically relevant compounds by promoting the azidation of a
- the need for directing groups, presenting a broad scope and satisfactory yields. The late-stage modification of complex molecules like (+)-artemisinin (69) and a (+)-tetrahydrogibberellic acid analogue 70 could be rapidly achieved in moderate yields (Scheme 25C). In 2014, Brown and Rasik employed
- the late-stage modification of amino acids and peptides in 2016 (Scheme 27A and B) [159]. The methodology facilitated the targeted C–H oxidative modifications in amino acids and peptides concomitant with the preservation of the α-center chirality in good yields and broad scope regarding the number of
Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs
Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122
- ruled out. Manganese-catalyzed late-stage C–H allylation The late-stage modification of peptides has received increasing attention due to the convenient and efficient modality. However, such protocols generally require substrate prefunctionalization and expensive metal catalysts, such as Pd [66][67][68
Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines
Beilstein J. Org. Chem. 2021, 17, 485–493, doi:10.3762/bjoc.17.42
- simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products. Keywords: amination; heteroarylation; quinoline N-oxides; regioselective; triazoles; Introduction Quinoline is a key heterocyclic moiety found in many
- transformation for late-stage modification of complex natural products was explored, and as shown in Scheme 4, the protocol was tested with various natural-product-derived triazoles. Novel C2-triazolyl products 4a–c were synthesized in good yield of 61–70% from triazoles derived from thymol, cholesterol and
- scaffolds. The late-stage modification of natural products is the salient feature of this current transformation. Experimental General procedure for the C2-selective synthesis of α-triazolylquinolines 3 To an oven-dried reaction tube equipped with a magnetic stirring bar were added quinoline N-oxide (1a, 29
Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst
Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16
- successful with a bromo-substituted substrates 3e and 3f, demonstrating that the methodology was suitable for substrates with the potential for further late-stage modification. Steric effects were also explored with C2-substituted substrate 3i and 3j, and no significant decline in product formation was
Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis
Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128
- 98% to afford α-benzoyloxy propargylic derivatives 39. Again the strategy can be applied to the late-stage modification of steroids with high levels of diastereoselectivity. λ3-Iodane reagents: azidobenziodoxolone (ABX) and chlorobenziodoxolone In a similar manner to the previously described
- -stage modification of complex products such as steroids. On the other hand, both the alkyne and the iodoarene moiety can be modified through post-transformation reactions thereby increasing the molecular diversity accessible with this process. The mechanism of the reaction (Scheme 11b) would first
- benzoate motif and the alkynyl group are obtained from various acceptor or donor–acceptor diazo compounds 30, while the use of vinyldiazo derivatives 32 leads to enynes 33 arising from the vinylogous addition of the carboxylate. Significantly, the benzoyloxy-alkynylation reaction can be applied to the late
Evidence for an iterative module in chain elongation on the azalomycin polyketide synthase
Beilstein J. Org. Chem. 2016, 12, 2164–2172, doi:10.3762/bjoc.12.206
- very high intermodular sequence identity. The ebelactone PKS from our data is faithfully colinear. We have previously reported the DNA sequence of both the azalomycin (azl) and kanchanamycin (kch) clusters [36]. Unlike ebelactone, these marginolactones undergo late-stage modification, including
Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation
Beilstein J. Org. Chem. 2013, 9, 1135–1140, doi:10.3762/bjoc.9.126
- -stage modification of the A ring motif of 7 that requires additional steps for the synthesis of the target molecules. In an effort to overcome this issue, we describe here a second-generation strategy of framework 9 in which the C-1 center has been methylated early in the synthesis. As such, it
- efficient construction of the tetracyclic core presents the principal challenge [19][20][21][22][23]. We have recently reported a unified synthetic strategy of 2, 3 and designed analogues using scaffold 7 as the key intermediate (Figure 2) [24][25][26]. A potential drawback of this strategy is the late
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