Gold Approaches to Polycyclic Indole Alkaloids

Barbour, P. Michael; Marholz, Laura J.; Chang, Le; Xu, Wenqing; Wang, Xiang

doi:10.1246/cl.131230

Cited by 48 publications

(16 citation statements)

References 49 publications

(19 reference statements)

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“…Platinum/gold catalysis has proved well suited for tandem cyclizations of alkynyl indoles; [30-35] in our previous work, we found triphenylphosphinegold(I) bis(trifluoromethane-sulfonyl)imidate (Ph 3 PAuNTf 2 ) to be an efficient catalyst for the tandem cyclization of alkynyl indoles 5 . [16, 17, 36] We first evaluated this catalyst in our initial attempt to cyclize 8a .…”

Section: Resultsmentioning

confidence: 99%

Property‐Guided Synthesis of Aza‐Tricyclic Indolines: Development of Gold Catalysis En Route

et al. 2016

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Antibiotic resistance is a worldwide public health threat that needs to be addressed by improved antibiotic stewardship and continuing development of new chemical entities to treat resistant bacterial infections. Compounds that work alongside known antibiotics as combination therapies offer an efficient and sustainable approach to counteract antibiotic resistance in bacteria. Guided by property-based analysis, a series of aza-tricyclic indolines (ATIs) were synthesized to optimize their physiochemical properties as novel combination therapies with β-lactams to treat methicillin-resistant S. aureus (MRSA) infections. A novel and highly efficient gold-catalyzed tandem cyclization was developed to facilitate the synthesis of these ATIs. One guanidine-containing ATI was discovered to possess both improved anti-MRSA activity and lower mammalian toxicity both in vitro and in vivo. In addition, it also showed significantly enhanced aqueous solubility and metabolic stability. These results indicated that the ATIs are a novel class of anti-MRSA agents suitable for further evaluations as adjuvant therapy in animal model studies.

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Section: Resultsmentioning

confidence: 99%

Property‐Guided Synthesis of Aza‐Tricyclic Indolines: Development of Gold Catalysis En Route

et al. 2016

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“…As a part of our ongoing research on gold catalysis 16 and merged organo/gold catalysis, 17 we envisaged that the Friedel-Crafts type reaction between 3-indolyl alcohols 1 and 2-alkynylidoles 2 would provide the corresponding indolyl-alkynes, which in the presence of appropriate Au-catalysts would afford bis-indoles in an apparently very simple way (Scheme 1b). Though there exists several reports on the indole-alkyne chemistry, 18 there is no precedence on the synthesis of desired bisindoles through proposed design. 19 Herein, we report a facile approach to access annulated bis-indoles from (1H-indol-3yl)(aryl)methanols and 2-(arylethynyl)-1H-indoles in the presence of Ph 3 PAuOTf/Brønsted acid binary catalyst system.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of annulated bis-indoles through Au(i)/Brønsted acid-catalyzed reactions of (1H-indol-3-yl)(aryl)methanols with 2-(arylethynyl)-1H-indoles

2017

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A general method to access annulated bis-indoles from (1H-indol-3-yl)(aryl)methanols and 2-(arylethynyl)-1H-indoles under the catalysis of the PhPAuOTf/Brønsted acid binary catalyst system has been developed. The reaction was found to proceed in a highly efficient manner and benefit from easy-to-make starting materials, broad substrate scope and operational simplicity. The potential of this method has also been exemplified for the synthesis of pyrrole-annulated indoles using 2-(phenylethynyl)-1H-indoles and phenyl(1H-pyrrol-2-yl)methanols. Furthermore, the use of a ternary catalyst system, involving PdCl/Brønsted acid/PhPAuOTf catalysts, has been realized for the synthesis of annulated bis-indoles starting directly from 2-(phenylbuta-1,3-diyn-1-yl)aniline and (1H-indol-3-yl)(aryl)methanol. Mechanistically, this reaction is very interesting since the overall process involves three different catalytic cycles catalyzed by three different catalysts in a relay fashion.

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“…Given several reviews in the period 2011 through 2014 on gold-catalyzed indole synthesis [1][2][3][4], this chapter focuses on a few seminal papers and then very recent work.…”

mentioning

confidence: 99%

Gold‐Catalyzed Indole Ring Synthesis

Gribble

2016

Indole Ring Synthesis

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Gold Approaches to Polycyclic Indole Alkaloids

Cited by 48 publications

References 49 publications

Property‐Guided Synthesis of Aza‐Tricyclic Indolines: Development of Gold Catalysis En Route

Property‐Guided Synthesis of Aza‐Tricyclic Indolines: Development of Gold Catalysis En Route

Synthesis of annulated bis-indoles through Au(i)/Brønsted acid-catalyzed reactions of (1H-indol-3-yl)(aryl)methanols with 2-(arylethynyl)-1H-indoles

Gold‐Catalyzed Indole Ring Synthesis

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