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Synlett 2013; 24(14): 1757-1771
DOI: 10.1055/s-0033-1339331
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© Georg Thieme Verlag Stuttgart · New York

Constructing Molecular Complexity from Alkynol Derivatives: A Journey from Fischer Carbene Complexes to Tandem Catalysis with Gold and other Carbophilic Lewis Acids

Félix Rodríguez*
Instituto Universitario de Química Organometálica ‘Enrique Moles’, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain   Fax: +34(985)103446   eMail: frodriguez@uniovi.es   eMail: fjfv@uniovi.es
,
Francisco J. Fañanás*
Instituto Universitario de Química Organometálica ‘Enrique Moles’, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain   Fax: +34(985)103446   eMail: frodriguez@uniovi.es   eMail: fjfv@uniovi.es
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Publikationsverlauf

Received: 02. Mai 2013

Accepted after revision: 05. Juni 2013

Publikationsdatum:
08. August 2013 (online)

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Abstract

One of the main challenges that organic chemists face is the development of new ways to obtain novel compounds in a fast, clean, and efficient manner. Among the strategies developed to achieve this goal are multicomponent and tandem reactions, which offer the opportunity of building up complex molecules from simple starting materials in a single synthetic operation. Alkynol derivatives are one example of these simple starting materials which, combined with other appropriate reagents, are easily transformed into interesting final products.

The explosion of research that has occurred in recent years in the field of gold catalysis has served to further raise the value of alkynol derivatives as useful materials for multicomponent and cascade reactions. This account describes our recent work in this area and shows how simple reagents can be catalytically converted into complex molecules containing interesting motifs, such as eight-membered rings, [3.3.1]- and [3.2.1]-bicyclic compounds, quinolines, and spiroacetals. In addition, the application of the methods developed is shown in the total syntheses of some natural products, such as berkelic acid.

1 Introduction

2 Synthesis of Eight-Membered Rings by a Pentacarbonyltungsten-Catalyzed Reaction

3 Synthesis of endo- and exo-Cyclic Enol Ethers by Pentacarbonyltungsten-Catalyzed Reactions and an Application of Such Compounds

4 Gold- and Platinum-Catalyzed Cascade Reactions Involving Allyl-Substituted Alkynol Derivatives

5 Intramolecular Hydroalkoxylation/Hydroarylation Reactions; Application to the Synthesis of Bruguierol A

6 Intermolecular Hydroalkoxylation/Hydroarylation Reactions; Synthesis of Bis(indolyl)alkanes and Intramolecular Redox Processes

7 Synthesis of Quinolines through a Multicomponent Cascade Process Involving a Povarov Reaction

8 Synthesis of Chroman Spiroacetals by a Multicomponent Cascade Reaction; Total Synthesis of (–)-Berkelic Acid

9 Enantioselective Synthesis of Spiroacetals by a Multicomponent Coupling Reaction

10 Cascade Hydroalkoxylation/Diels–Alder Reactions

11 Outlook

Key words

alkynols - gold - multicomponent reactions - tandem catalysis - tungsten