Syntheses of Post-Iboga Alkaloids

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