2017
DOI: 10.1021/acs.chemrev.7b00022
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Applications of Nonenzymatic Catalysts to the Alteration of Natural Products

Abstract: The application of small molecules as catalysts for the diversification of natural product scaffolds is reviewed. Specifically, principles that relate to the selectivity challenges intrinsic to complex molecular scaffolds are summarized. The synthesis of analogs of natural products by this approach is then described as a quintessential “late-stage functionalization” exercise wherein natural products serve as the lead scaffolds. Given the historical application of enzymatic catalysts to the site-selective alter… Show more

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Cited by 181 publications
(127 citation statements)
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“…1 Although efficient in principle, this approach necessarily confronts a series of challenges, including (a) the compatibility of the reagents and reaction conditions with a highly functionalized substrate and (b) the site- and stereoselectivity with which reactions occur. 1 Nonetheless, a growing number of reports have demonstrated the potential to achieve catalyst-controlled, site- and, when applicable, stereoselective functionalizations of several functional groups present in biologically relevant compounds. 2 …”
Section: Introductionmentioning
confidence: 99%
“…1 Although efficient in principle, this approach necessarily confronts a series of challenges, including (a) the compatibility of the reagents and reaction conditions with a highly functionalized substrate and (b) the site- and stereoselectivity with which reactions occur. 1 Nonetheless, a growing number of reports have demonstrated the potential to achieve catalyst-controlled, site- and, when applicable, stereoselective functionalizations of several functional groups present in biologically relevant compounds. 2 …”
Section: Introductionmentioning
confidence: 99%
“…Structure diversification of polyfunctional scaffolds in a chemo‐ or site‐selective fashion has emerged as a highly efficient chemical approach for drug discovery efforts . Such strategies allow organic/medicinal chemists to generate a library of novel structural analogs very rapidly, and without the need for extensive protective group manipulation .…”
Section: Introductionmentioning
confidence: 99%
“…Structure diversification of polyfunctional scaffolds in a chemoor site-selective fashion has emerged as a highly efficient chemical approach for drug discovery efforts. [1][2][3] Such strategies allow organic/medicinal chemists to generate a library of novel structural analogs very rapidly, and without the need for extensive protective group manipulation. [4][5][6] Nitrogen containing heterocyclic compounds, including indole, benzimidazole and indolylbenzimidazoles are an important class of bioactive scaffolds due to their broad spectrum of bioactivity.…”
Section: Introductionmentioning
confidence: 99%
“…[1a] Although site-specific modification of 1 is ap ossible approach for improving its aqueous solubility,a rchitectural complexity and ah igh density of delicate functionalities provide af ormidable barrier to successful, site-selective chemical modification. [3,4] Thedehydroalanine (Dha) residues characteristic of 1 and other thiopeptides are reactive sites,most notably as Michael acceptors for av ariety of nucleophilic species. [5] Previously, several studies have been carried out on additions to the Dha residues in 1 (Figure 1, middle).…”
Section: Introductionmentioning
confidence: 99%