Gold-Catalyzed Cyclizations of Alkynol-Based Compounds: Synthesis of Natural Products and Derivatives

Abstract

The last decade has witnessed dramatic growth in the number of reactions catalyzed by gold complexes because of their powerful soft Lewis acid nature. In particular, the gold-catalyzed activation of propargylic compounds has progressively emerged in recent years. Some of these gold-catalyzed reactions in alkynes have been optimized and show significant utility in organic synthesis. Thus, apart from significant methodology work, in the meantime gold-catalyzed cyclizations in alkynol derivatives have become an efficient tool in total synthesis. However, there is a lack of specific review articles covering the joined importance of both gold salts and alkynol-based compounds for the synthesis of natural products and derivatives. The aim of this Review is to survey the chemistry of alkynol derivatives under gold-catalyzed cyclization conditions and its utility in total synthesis, concentrating on the advances that have been made in the last decade, and in particular in the last quinquennium.

Highly Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles Using Au(I) Catalyzed Oxidation System at Room Temperature

“…The resulting crude reaction mixture was purified by silica gel flash chromatography to afford 4. 1 H, 13 C NMR spectra, Fourier Transform infrared spectroscopy (FTIR), and Electrospray Ionization (ESI) for products 4 are consistent with the literature [10,11].…”

“…In the past two decades, homogenous gold complexes were gradually believed to be an active catalyst, and it had been used in many reactions, such as forming reactions for C-C and C-O bonds, hydrogenation, and oxidation [12,13]. Noticeably, various gold catalysts with different ligands and counter anions showed high efficiency in the activation of a C-C triple bond in alkyne via nucleophilic addition.…”

Synthesis of Gold Catalysts Supported on Mesoporous Silica Materials: Recent Developments

“…Because of the large number of available literature and applications, neither the characterization methods of the synthesized gold catalysts nor the physical chemistry of the catalytic reactions is covered in this review. Readers interested on these topics can find useful information in this special issue of Catalysts, in the recent thematic issue of the Chemical Society Reviews (2008 Gold: Chemistry, Materials and Catalysis issue), and in the current specific literature [5,35,40,50].…”

Gold-catalyzed C–O bond forming reactions for the synthesis of six-membered O-heterocycles

“…Scheme 20 obtained by Au-catalyzed cycloisomerization of alkynediols along with benzofuran in notable amounts [159].…”