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Total Synthesis of Indole Alkaloids

Total Synthesis of Indole Alkaloids

Based on Direct Construction of Pyrrolocarbazole Scaffolds Via Gold-Catalyzed Cascade Cyclizations

by Junpei Matsuoka
Paperback
Publication Date: 20/09/2021

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This book explores efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations, presenting two strategies for total synthesis of these natural products based on gold-catalyzed reactions of conjugated diyne or ynamide. 

The book first describes the total and formal synthesis of dictyodendrins A-F based on direct construction of the pyrrolo[2,3-c]carbazole core using the gold-catalyzed annulation of azido-diynes and protected pyrrole. This synthetic strategy features late-stage functionalization of the pyrrolo[2,3-c]carbazole scaffold at several positions and allows diverse access to dictyodendrins and their derivatives. Secondly, the book discusses the formal synthesis of vindorosine based on the pyrrolo[2,3-d]carbazole construction using the gold-catalyzed cascade cyclization of ynamide. Importantly, the reaction using a chiral gold complex provides the optically active pyrrolo[2,3-d]carbazole. This strategy facilitates the rapid construction of the pyrrolocarbazole core structure of aspidosperma and related alkaloids, including vindorosine. 

These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds.

ISBN:
9789811586545
9789811586545
Category:
Pharmaceutical technology
Format:
Paperback
Publication Date:
20-09-2021
Language:
English
Publisher:
Springer
Country of origin:
United States
Dimensions (mm):
235x155mm
Weight:
0.16kg

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