Total Synthesis of Indole Alkaloids

1. Front Matter

   Pages i-xii

   PDF

2. Introduction

   • Junpei Matsuoka

   Pages 1-18

3. Total Synthesis of Dictyodendrins by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles

   • Junpei Matsuoka

   Pages 19-65

4. Construction of the Pyrrolo[2,3-d]Carbazole Core of Spiroindoline Alkaloids by Gold-Catalyzed Cascade Cyclization of Ynamide

   • Junpei Matsuoka

   Pages 67-79

5. Conclusion

   • Junpei Matsuoka

   Pages 81-82

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.

• Gold Catalysis
• Total Synthesis of Dictyodendrin
• Pyrrolocarbazole
• Cascade Reaction
• Indole Alkaloid
• Natural Product Synthesis

• Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts, Kyotanabe, Japan

  Junpei Matsuoka

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. 

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