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.

With its impressive features, gold has led to completely new reaction types in recent years, which in turn have strongly influenced both organic catalysis and material science. Other fields where a significant amount of new results has been obtained include nanotechnology, self assembly/supramolecular systems and biochemical/medicinal chemistry. As a result, gold is one of the hottest topics in catalysis at the moment, with an increasing amount of research being carried out in this field. While focusing on homogeneous catalysis, this monograph also covers the main applications in heterogeneous catalysis. Following a look at the gold-catalyzed addition of heteroatom nucleophiles to alkynes, it goes on to discuss gold-catalyzed additions to allenes and alkenes, gold-catalyzed benzannulations, cycloisomerization and rearrangement reactions, as well as oxidation and reduction reactions. The whole is finished off with a section on gold-catalyzed aldol and related reactions and the application of gold-catalyzed reactions to natural product synthesis. Of interest to synthetic chemists and inorganic chemists, as well as organic chemists working in homogeneous catalysis, physical and technical chemists.

Gold has traditionally been regarded as inactive as a catalytic metal. However, the advent of nanoparticulate gold on high surface area oxide supports has demonstrated its high catalytic activity in many chemical reactions. Gold is active as a heterogeneous catalyst in both gas and liquid phases, and complexes catalyse reactions homogeneously in solution. Many of the reactions being studied will lead to new application areas for catalysis by gold in pollution control, chemical processing, sensors and fuel cell technology. This book describes the properties of gold, the methods for preparing gold catalysts and ways to characterise and use them effectively in reactions. The reaction mechanisms and reasons for the high activities are discussed and the applications for gold catalysis considered. Sample Chapter(s). Chapter 1: Introduction to Catalysis (892 KB). Contents: Introduction to Catalysis; The Physical and Chemical Properties of Gold; Physical Properties and Characterisation of Small Gold Particles; Preparation of Supported Gold Catalysts; Chemisorption of Simple Molecules on Gold; Oxidation of Carbon Monoxide; The Selective Oxidation of Carbon Monoxide; Selective Oxidation; Reactions Involving Hydrogen; The WaterOCoGas Shift; Reactions of Environmental Importance; Catalysis by Soluble and Supported Gold Compounds; Miscellaneous Reactions Catalysed by Gold; Commercial Applications. Readership: Postgraduate level researchers in academia and industry, as well as general readers."

Research on designing new catalytic systems has been one of the most important fields in modern organic chemistry, and one reason for this is the predominant contribution of catalysis to the concepts of atom economy and green chemistry in the 21st century. Gold, considered catalytically inactive for a long time, is now a fascinating partner of modern chemistry, as scientists such as Bond, Haruta, Hutchings, Ito and Hayashi opened new perspectives for the whole synthetic chemist community. This book presents the major advances in homogeneous catalysis, emphasizing the methodologies that create carbon-carbon and carbon-heteroatom bonds, the applications that create diversity and synthesize natural products, and the recent advances and challenges in asymmetric catalysis and computational research. The Handbook of Homogeneous Gold Catalysis provides readers with in-depth information about gold-catalyzed reactions and presents several explanations for the scientific design of a catalyst. Readers will be able to understand the entire gold area and find solutions to problems in catalysis. Featuring prominent authors, who are experts in their respective fields, this is the first book dedicated to homogeneous gold chemistry. Contents: From Gold in Nature to Gold Catalysts (S Kramer and F Gagosz); Oxidation and Reduction Reactions (L Zhang); Gold-Catalyzed Addition of Carbon Nucleophile to C-C Multiple Bond (B Simmons and H C Shen); Gold-Catalyzed Addition of Heteroatom Nucleophile to C-C Multiple Bond (N Asao, N Hatakeyama and Y Yamamoto); Gold-Catalyzed Synthesis of Heterocycles (A Arcadi); Multi-Component Reactions (R Skouta and C J Li); Gold Catalyzed Tandem and Cascade Reactions (R-S Liu); Cycloisomerization Reactions of 1, n -Enynes (N Huguet and A Echavarren); Gold-Catalyzed Reaction of Propargylic Esters (L Fensterbank, J-P Goddard, M Malacria and S Simonneau); Gold-Catalyzed Cross-Coupling Reactions (S Blum); Gold-Catalyzed Reactions: A Computational Approach (E Soriano & J Marco-Contelles); Asymmetric Gold-Catalyzed Reactions (P Y Toullec, A Pradal and V Michelet); Gold Catalysis in Natural Product Synthesis (M Gesinski and F D Toste). Readership: Student, professionals.

Research on designing new catalytic systems has been one of the most important fields in modern organic chemistry. One reason for this is the predominant contribution of catalysis to the concepts of atom economy and green chemistry in the 21st century. Gold, considered catalytically inactive for a long time, is now a fascinating partner of modern chemistry, as scientists such as Bond, Teles, Haruta, Hutchings, Ito and Hayashi opened new perspectives for the whole synthetic chemist community. This book presents the major advances in homogeneous catalysis, emphasizing the methodologies that create carbon-carbon and carbon-heteroatom bonds, the applications that create diversity and synthesize natural products, and the recent advances and challenges in asymmetric catalysis and computational research.It provides readers with in-depth information about homogeneous gold-catalyzed reactions and presents several explanations for the scientific design of a catalyst. Readers will be able to understand the entire gold area and find solutions to problems in catalysis.Gold Catalysis — An Homogeneous Approach is part of the Catalytic Science Series and features prominent authors who are experts in their respective fields.

This book explores efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations, presenting two strategies for total synthesis of these natural products based on gold-catalyzed reactions of conjugated diyne or ynamide. The book first describes the total and formal synthesis of dictyodendrins A–F based on direct construction of the pyrrolo[2,3-c]carbazole core using the gold-catalyzed annulation of azido-diynes and protected pyrrole. This synthetic strategy features late-stage functionalization of the pyrrolo[2,3-c]carbazole scaffold at several positions and allows diverse access to dictyodendrins and their derivatives. Secondly, the book discusses the formal synthesis of vindorosine based on the pyrrolo[2,3-d]carbazole construction using the gold-catalyzed cascade cyclization of ynamide. Importantly, the reaction using a chiral gold complex provides the optically active pyrrolo[2,3-d]carbazole. This strategy facilitates the rapid construction of the pyrrolocarbazole core structure of aspidosperma and related alkaloids, including vindorosine. These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds.

The amaryllidaceae family is an attractive source of alkaloids, which are valuable targets for total synthesis. This thesis describes the ingenious approach to the synthesis of two amaryllidaceae alkoids: (+/-)-lycorine and gracilamine. Utilization of the phenylbutadiene and pyrroline intramolecular push-pull Diels-Alder reaction for lycorine and of the intramolecular 1,3-dipolar cycloaddition for gracilamine is described. A route was developed to give access to advanced intermediates required for both syntheses. However the existing methodology did not fully accommodate the complete core structure of the targets. Development of a new novel gold-catalyzed reaction is also depicted. A facile and quick method to generate dienes from propargylic acetates and pyvaloates has been developed. The scopes and limitations of this methodology are discussed. The application of the newly discovered Au(PPh3)Cl and acid catalyst system was examined. Finally, we investigated the 1-alkynyl-2-vinyl-cyclohexanols for the formation of multi-cyclic skeletons found in natural products. Our goal was to develop a way to easily access the steroid and/or carbocyclic core in one tandem reaction sequence. To this end, the use of a tandem oxy-cope/Claisen/ene/Diels-Alder reaction was developed. The tandem oxy-Cope/Claisen/ene/Diels-Alder reaction can produce up to 9 contiguous stereogenic centers where two are quaternary. In addition, this domino process provides the steroid core possessing much exploitable functionality.