The Akuammiline Alkaloids; Origin and Synthesis

Ruben Eckermann; Tanja Gaich

doi:10.1055/s-0033-1339711

Synthesis, Table of Contents

Synthesis 2013; 45(20): 2813-2823
DOI: 10.1055/s-0033-1339711

short review

The Akuammiline Alkaloids; Origin and Synthesis

Ruben Eckermann

Institute of Organic Chemistry, University of Hannover, Schneiderberg 1, 30167 Hannover, Germany Fax: +49(511)7623011 Email: tanja.gaich@oci.uni-hannover.de

,

Tanja Gaich*

Institute of Organic Chemistry, University of Hannover, Schneiderberg 1, 30167 Hannover, Germany Fax: +49(511)7623011 Email: tanja.gaich@oci.uni-hannover.de

› Author Affiliations

Abstract

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Abstract

Due to their structural diversity, elegant polycyclic molecular architecture, and biological activity, the indole alkaloids have been investigated by organic chemists over the last century. The first akuammiline alkaloid, echitamine, was isolated in 1875 and first described in 1880. Owing to the exceptional structure of akuammiline alkaloids, it was not until 125 years later that the first successful total synthesis was accomplished. This review will give an overview of this class of alkaloids, pinpointing its structural characteristics and showcasing the completed total syntheses. Furthermore, an overview of the structural diversity is given.

1 Introduction

2 Structural Analysis

3 Biosynthesis

4 Completed Total Syntheses

4.1 (±)-Vincorine

4.2 (–)-Vincorine

4.3 (±)-Aspidophylline A

4.4 (+)-Scholarisine A

5 Conclusion

Key words

alkaloids - biosynthesis - indoles - natural products - polycycles

Full Text

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