Gold-Catalyzed Cycloisomerization of <i>N</i>-Propargylindole-2-carboxamides: Application toward the Synthesis of Lavendamycin Analogues

England, Dylan B.; Padwa, Albert

doi:10.1021/ol801385h

Cited by 118 publications

(38 citation statements)

References 64 publications

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“…Padwa and collaborators, for example, reported the gold-promoted cycloisomerization of N-propargylindole-2-carboxamides to yield -carbolinones, which were further functionalized to prepare natural product analogues, [65,66] whereas Liu's group reported the synthesis of highly functionalized tetrahydrocarbazoles through gold-catalyzed deacylative cycloisomerization of 3-acylindole-2-ynes. Padwa and collaborators, for example, reported the gold-promoted cycloisomerization of N-propargylindole-2-carboxamides to yield -carbolinones, which were further functionalized to prepare natural product analogues, [65,66] whereas Liu's group reported the synthesis of highly functionalized tetrahydrocarbazoles through gold-catalyzed deacylative cycloisomerization of 3-acylindole-2-ynes.…”

Section: Scheme 16 Synthesis Of Indoloazepinones 41mentioning

confidence: 99%

Gold‐Catalyzed Functionalization Reactions of Indole

Pirovano

2018

Eur J Org Chem

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This review summarizes the progress achieved in the last fifteen years by application of homogeneous gold catalysis in the field of indole functionalization. Several electrophilic species obtained through gold‐catalyzed π‐activation have in fact been found to react with the nucleophilic positions of indole, thus allowing its efficient manipulation. In order to furnish a complete and clear overview on the role of the catalyst, the review is organized from the perspective of the gold‐activated substrate that is reacting with the indole. In addition, in view of the ability of gold to catalyze tandem and cascade reactions, a separate section describes tandem/cascade protocols useful for the synthesis of complex polycyclic indole derivatives. Finally, gold catalysis has also been employed for the synthesis of indole‐based natural products. For this reason, a dedicated section collects all the work in which the key step to obtain these complex indoles is represented by a gold‐catalyzed reaction.

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Section: Scheme 16 Synthesis Of Indoloazepinones 41mentioning

confidence: 99%

Gold‐Catalyzed Functionalization Reactions of Indole

Pirovano

2018

Eur J Org Chem

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“…Step 1 is a 6‐ exo ‐dig cyclization followed by isomerization leading to the new β‐carbolinone 9 . A similar electrophilic activation of monoalkynes by gold(III) was described by England and Padwa by using AuCl 3 . Step 2 is a novel 6‐ endo ‐dig cyclization towards 4 H ‐quinolizin‐4‐one 10 , inspired by the synthesis of a related regioisomer .…”

Section: Resultsmentioning

confidence: 96%

Photoreduction of Thioether Gold(III) Complexes: Mechanistic Insight and Homogeneous Catalysis

Cao

Bassani

Bibal

2018

Chemistry A European J

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Complexes formed between AuCl3 and thioether ligands underwent a photoinduced reductive elimination under homogeneous conditions in dichloromethane and toluene solutions to afford the corresponding AuI complexes. All the gold(III) complexes were rapidly reduced to the gold(I) chloride complexes under 365 nm irradiation or ambient light while being thermally stable below 55 °C. The mechanism of photoreduction through Cl2 elimination is discussed based on a kinetic study and the chemical trapping of chlorine species: Cl2, radical Cl., and possibly Cl+. The catalytic activities of the gold(III) chloride complexes and the corresponding gold(I) complexes obtained by in situ reduction were evaluated in the cyclization of N‐propargylic amides to oxazoles. The merits of such photoreducible complexes in homogeneous gold catalysis are illustrated by a cascade reaction catalyzed by thioether gold complexes that affords a 4H‐quinolizin‐4‐one in high yields.

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“…This cyclizationrearomatization strategy has demonstrated diverse applications such as the development of regiodivergent pathways, 19,20 diversity-oriented pathways, 21 syntheses of natural products such as lavendamycin analogues, 22 as well as tandem intermolecular annulations. 23 …”

Section: Cyclization-rearomatization Strategymentioning

confidence: 99%

Gold Approaches to Polycyclic Indole Alkaloids

et al. 2014

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Indole alkaloids are a highly diverse and ubiquitous family of natural products often identified in plants that have been used as traditional medicine for millennia. Because of their complex molecular architecture and relevance as potent pharmaceuticals, efficient methods for constructing these polycyclic skeletons are essential for their synthesis. Herein, we review recent developments in gold catalysis as a means toward the synthesis of many biologically important polycyclic indole alkaloids.

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Gold-Catalyzed Cycloisomerization of N-Propargylindole-2-carboxamides: Application toward the Synthesis of Lavendamycin Analogues

Cited by 118 publications

References 64 publications

Gold‐Catalyzed Functionalization Reactions of Indole

Gold‐Catalyzed Functionalization Reactions of Indole

Photoreduction of Thioether Gold(III) Complexes: Mechanistic Insight and Homogeneous Catalysis

Gold Approaches to Polycyclic Indole Alkaloids

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