DNA-Templated [2+2] Photocycloaddition: A Straightforward Entry into the Aplysinopsin Family of Natural Products
العنوان: | DNA-Templated [2+2] Photocycloaddition: A Straightforward Entry into the Aplysinopsin Family of Natural Products |
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المؤلفون: | Erwan Poupon, Stellios Arseniyadis, Michael Smietana, Jean-Jacques Vasseur, Mehdi A. Beniddir, Adam Skiredj, Nicolas Duchemin, Karine Leblanc, Laurent Evanno, Justine Mansot |
المساهمون: | Queen Mary University of London (QMUL), Molécules bioactives, conception, isolement et synthèse (MBCIS), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Équipe 'Pharmacognosie-Chimie des Substances Naturelles' BioCIS, Centre National de la Recherche Scientifique (CNRS), School of Biological and Chemical Sciences, Queen Mary University of London, ANR-15-CE29-0021,D-CYSIV,Stratégie innovante pour la catalyse asymétrique à base d'ADN(2015), ANR-11-IDEX-0003,IPS,Idex Paris-Saclay(2011), Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11), Laboratoire d'océanographie et de biogéochimie (LOB), Université de la Méditerranée - Aix-Marseille 2-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), ANR-15-CE29-0021,D-CYSIV,Stratégie innovante pour la catalyse asymétrique à base d’ADN(2015), ANR-11-IDEX-0003-02/10-LABX-0033,LERMIT,Research Laboratory on Drugs and Therapeutic Innovation(2011) |
المصدر: | Angewandte Chemie International Edition Angewandte Chemie International Edition, Wiley-VCH Verlag, 2018, 57 (36), pp.11786-11791. ⟨10.1002/anie.201806357⟩ |
بيانات النشر: | Wiley, 2018. |
سنة النشر: | 2018 |
مصطلحات موضوعية: | [CHIM.THER]Chemical Sciences/Medicinal Chemistry, STONY CORAL, 010402 general chemistry, 01 natural sciences, Cyclobutane, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, BINDING, [CHIM]Chemical Sciences, Olefin fiber, Natural product, CATALYSIS, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, PHOTOCHEMISTRY, GUANIDINIUM, Total synthesis, PHOTOREACTIONS, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, General Medicine, Combinatorial chemistry, Cycloaddition, DIMERS, 0104 chemical sciences, Aplysinopsin, chemistry, SELECTIVITY, ALKALOIDS, COMPLEXES, Selectivity, DNA |
الوصف: | International audience; Biosynthetic considerations inspired us to harness the templating properties offered by DNA to promote a [2+2] photoinduced cycloaddition. The method was developed based on the dimerization of (E)-aplysinopsin, which was previously shown to be unproductive in solution. In sharp contrast, exposure of this tryptophan-derived olefin to light in the presence of salmon testes DNA (st-DNA) reproducibly afforded the corresponding homo-dimerized spiro-fused cyclobutane in excellent yields. DNA provides unique templating interactions enabling a singular mimic of the solid-state aggregation necessary for the [2+2] photocycloaddition to occur. This method was ultimately used to promote the prerequisite dimerizations leading to both dictazole B and tubastrindole B, thus constituting the first example of a DNA-mediated transformation to be applied to the total synthesis of a natural product. |
تدمد: | 0044-8249 1433-7851 1521-3773 |
URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::579409a60322ba766eb087074327a6cf https://doi.org/10.1002/ange.201806357 |
حقوق: | OPEN |
رقم الأكسشن: | edsair.doi.dedup.....579409a60322ba766eb087074327a6cf |
قاعدة البيانات: | OpenAIRE |
تدمد: | 00448249 14337851 15213773 |
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