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      Unconventional Macrocyclizations in Natural Product Synthesis

      , , , ,

      ACS Central Science

      American Chemical Society

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          Abstract

          Over the past several decades, macrocyclic compounds have emerged as increasingly significant therapeutic candidates in drug discovery. Their pharmacological activity hinges on their rotationally restricted three-dimensional orientation, resulting in a unique conformational preorganization and a high enthalpic gain as a consequence of high-affinity macrocycle–protein binding interactions. Synthetic access to macrocyclic drug candidates is therefore crucial. From a synthetic point of view, the efficiency of macrocyclization events commonly suffers from entropic penalties as well as undesired intermolecular couplings (oligomerization). Although over the past several decades ring-closing metathesis, macrolactonization, or macrolactamization have become strategies of choice, the toolbox of organic synthesis provides a great number of versatile transformations beyond the aforementioned. This Outlook focuses on a selection of examples employing what we term unconventional macrocyclizations toward the synthesis of natural products or analogues.

          Abstract

          Unconventional retrosynthetic disconnections enable novel approaches to the synthesis of macrocyclic natural products. Several examples spanning the spectrum of organic chemistry are presented.

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          The heck reaction as a sharpening stone of palladium catalysis.

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            Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation.

            Metal-catalysed C-H bond functionalisation has had a significant impact on how chemists make molecules. Translating the methodological developments to their use in the assembly of complex natural products is an important challenge for the continued advancement of chemical synthesis. In this tutorial review, we describe selected recent examples of how the metal-catalysed C-H bond functionalisation has been able to positively affect the synthesis of natural products.
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              Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

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                Author and article information

                Journal
                ACS Cent Sci
                ACS Cent Sci
                oc
                acscii
                ACS Central Science
                American Chemical Society
                2374-7943
                2374-7951
                21 September 2020
                25 November 2020
                : 6
                : 11
                : 1869-1889
                Affiliations
                []Institute of Organic Chemistry, University of Vienna , Währinger Strasse 38, 1090 Vienna, Austria
                []Research Platform for Next Generation Macrocycles , Währinger Strasse 38, 1090 Vienna, Austria
                Author notes
                Article
                10.1021/acscentsci.0c00599
                7706100

                This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.

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