Published as part of the Bürgenstock Special Section 2018 Future Stars in Organic Chemistry
This paper is dedicated to Prof. Byong-Seok Choi in memory of his retirement.
Abstract
Post-iboga alkaloids are secondary metabolites that are biosynthetically derived from iboga-type alkaloids via rearrangements of the indole and/or isoquinuclidine moieties. Herein, we categorize post-iboga alkaloids into five types based on the biosynthetic mode of transformation of the iboga scaffold. We then describe reported syntheses of post-iboga alkaloids, including our laboratory’s recent contributions, based on our own categorization.
1 Introduction
1.1 Iboga and Post-Iboga Alkaloids
1.2 Classification of Post-Iboga Alkaloids
1.2.1 Introduction to Type I Post-Iboga Alkaloids
1.2.2 Introduction to Type II Post-Iboga Alkaloids
1.2.3 Introduction to Type III Post-Iboga Alkaloids
1.2.4 Introduction to Type IV Post-Iboga Alkaloids
1.2.5 Introduction to Type V Post-Iboga Alkaloids
2 Syntheses of Post-Iboga Alkaloids
2.1 Syntheses of Type I Post-Iboga Alkaloids
2.1.1 Syntheses of Monomeric Type I Post-Iboga Alkaloids
2.1.2 Syntheses of Dimeric Type I Post-Iboga Alkaloids
2.2 Syntheses of Type II Post-Iboga Alkaloids
2.3 Synthetic Studies Toward Type III Post-Iboga Alkaloids
2.4 Syntheses of Type IV Post-Iboga Alkaloids
2.5 Synthesis of Type V Post-Iboga Alkaloids
3 Conclusion and Outlook
Key words
iboga alkaloids - post-iboga alkaloids - biosynthetic hypothesis - total synthesis - semi-synthesis
