Brønsted Acid‐Catalyzed Tandem Cyclizations of Tryptamine‐Ynamides Yielding 1H‐Pyrrolo[2,3‐d]carbazole Derivatives

Brønsted Acid‐Catalyzed Tandem Cyclizations of Tryptamine‐Ynamides Yielding... What is the most significant result of this study?The tandem cyclization strategy represents a unique and straightforward method to access a 1H‐pyrrolo[2,3‐d]carbazole scaffold, which is the core motif in a series of indole alkaloids. To construct the spiroindolines through the indoleninium intermediate, the inherent tendency of C−C bond migration through Wagner–Meerwein rearrangement to generate a tricyclic fused ring system was circumvented by an instantaneous intramolecular nucleophilic trap to indoleninium via an in situ formed enol species induced by the formation of a more stable conjugate diene moiety. It is expected that such a methodology will find broad applications in the syntheses of various indole alkaloids with 1H‐pyrrolo[2,3‐d]carbazole scaffolds.What was the inspiration for this cover design?Inspired by the ancient Chinese Movable Type, a famous Chinese invention from hundreds of years ago, in which the metal blocks can be used/reused to mass produce various books, our method makes it possible to synthesize various indole alkaloids from simple building blocks. We further depicted our work by combining traditional Chinese fine arts such as ink wash painting and Chinese calligraphy in the background with our newly developed methodology.What other topics are you working on at the moment?Our main research interest is focused on developing new methods to construct important scaffolds of biologically active natural products and heterocycles and on applying our methods to the total syntheses of natural products for the construction of small molecule libraries. This includes ynamide‐based tandem cyclizations to indole alkaloids, gold‐catalyzed pathway‐controllable synthesis to structurally diverse heterocycles as well as water‐resistant Lewis acid‐catalyzed organic reactions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Brønsted Acid‐Catalyzed Tandem Cyclizations of Tryptamine‐Ynamides Yielding 1H‐Pyrrolo[2,3‐d]carbazole Derivatives

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Publisher
Wiley Subscription Services, Inc., A Wiley Company
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
D.O.I.
10.1002/chem.201706015
Publisher site
See Article on Publisher Site

Abstract

What is the most significant result of this study?The tandem cyclization strategy represents a unique and straightforward method to access a 1H‐pyrrolo[2,3‐d]carbazole scaffold, which is the core motif in a series of indole alkaloids. To construct the spiroindolines through the indoleninium intermediate, the inherent tendency of C−C bond migration through Wagner–Meerwein rearrangement to generate a tricyclic fused ring system was circumvented by an instantaneous intramolecular nucleophilic trap to indoleninium via an in situ formed enol species induced by the formation of a more stable conjugate diene moiety. It is expected that such a methodology will find broad applications in the syntheses of various indole alkaloids with 1H‐pyrrolo[2,3‐d]carbazole scaffolds.What was the inspiration for this cover design?Inspired by the ancient Chinese Movable Type, a famous Chinese invention from hundreds of years ago, in which the metal blocks can be used/reused to mass produce various books, our method makes it possible to synthesize various indole alkaloids from simple building blocks. We further depicted our work by combining traditional Chinese fine arts such as ink wash painting and Chinese calligraphy in the background with our newly developed methodology.What other topics are you working on at the moment?Our main research interest is focused on developing new methods to construct important scaffolds of biologically active natural products and heterocycles and on applying our methods to the total syntheses of natural products for the construction of small molecule libraries. This includes ynamide‐based tandem cyclizations to indole alkaloids, gold‐catalyzed pathway‐controllable synthesis to structurally diverse heterocycles as well as water‐resistant Lewis acid‐catalyzed organic reactions.

Journal

Chemistry - A European JournalWiley

Published: Jan 15, 2018

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