New Gold-Catalyzed Reactions and Applications for the Synthesis of Alkaloids [electronic resource] / by Ana Escribano Cuesta.Material type: TextSeries: Springer Theses, Recognizing Outstanding Ph.D. Research: Publisher: Cham : Springer International Publishing : Imprint: Springer, 2013Description: XIII, 195 p. online resourceContent type: text Media type: computer Carrier type: online resourceISBN: 9783319007021Subject(s): Chemistry | Organic chemistry | Organometallic chemistry | Catalysis | Chemistry | Organometallic Chemistry | Catalysis | Organic ChemistryAdditional physical formats: Printed edition:: No titleDDC classification: 547.05 LOC classification: QD410-412.5Online resources: Texto completo
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Introduction -- General Objectives -- Gold(I)-Catalyzed Reactions of 1,6-Enynes with Aldehydes: Cycloaddition versus Metathesis-Type Reactions -- Formation of Cyclobutene Compounds via Gold(I)-Catalyzed Cycloisomerization of 1,n-Enynes -- Approach Toward the Total Synthesis of Lundurines.
Ana Escribano Cuesta's thesis presents a detailed study of the inter- and intramolecular reactions of carbonyl compounds with 1,6-enynes using gold (I) complexes. An important part of the work involved streamlining the variables that allow the selective synthesis of different products such as tricyclic compounds, dihydropyrans, 1,3-dienes or cyclobutenes. The second chapter highlights the importance and difficulties in synthesising a cyclobutene subunit and the author includes a detailed description of how the products were prepared. The final chapter outlines the synthesis of lundurines using methodology developed by the author's research group for intramolecular gold-catalyzed cyclization of indoles with alkynes. The lundurine products developed in this work show significant in vitro cytoxicity toward B16 melanoma cells. The work in this thesis has led to a number of publications in high-profile chemistry journals.