Springer Theses

Total Synthesis of Indole Alkaloids

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

Authors: Matsuoka, Junpei

Free Preview
  • Nominated as an outstanding Ph.D. thesis by Kyoto University 
  • Provides novel strategies for the construction of pyrrolocarbazole core structures 
  • Explains the design and development of divergent synthesis of natural products
see more benefits

Buy this book

eBook 117,69 €
price for Spain (gross)
  • ISBN 978-981-15-8652-1
  • Digitally watermarked, DRM-free
  • Included format: PDF, EPUB
  • Immediate eBook download after purchase and usable on all devices
  • Bulk discounts from 10 eBooks
Hardcover 145,59 €
price for Spain (gross)
About this book

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.

About the authors

Junpei Matsuoka is a research associate at the Department of Medicinal Chemistry, Doshisha Women's College of Liberal Arts. His research interests include the development of transition-metal-catalyzed reactions as well as the total synthesis of natural products. He received his bachelor’s degree from Meijo University in 2016 and his Ph.D. degree from Kyoto University in 2020. During his Ph.D. program, he was supported by a research fellowship for young scientists by the Japan Society for the Promotion of Science. He was awarded the Pharmaceutical Society of Japan Kansai Branch Award for Young Scientists. 

Table of contents (4 chapters)

Table of contents (4 chapters)

Buy this book

eBook 117,69 €
price for Spain (gross)
  • ISBN 978-981-15-8652-1
  • Digitally watermarked, DRM-free
  • Included format: PDF, EPUB
  • Immediate eBook download after purchase and usable on all devices
  • Bulk discounts from 10 eBooks
Hardcover 145,59 €
price for Spain (gross)
Loading...

Recommended for you

Loading...

Bibliographic Information

Bibliographic Information
Book Title
Total Synthesis of Indole Alkaloids
Book Subtitle
Based on Direct Construction of Pyrrolocarbazole Scaffolds via Gold-Catalyzed Cascade Cyclizations
Authors
Series Title
Springer Theses
Copyright
2020
Publisher
Springer Singapore
Copyright Holder
The Editor(s) (if applicable) and The Author(s), under exclusive license to Springer Nature Singapore Pte Ltd.
eBook ISBN
978-981-15-8652-1
DOI
10.1007/978-981-15-8652-1
Hardcover ISBN
978-981-15-8651-4
Series ISSN
2190-5053
Edition Number
1
Number of Pages
XII, 82
Number of Illustrations
73 b/w illustrations, 4 illustrations in colour
Topics