Syntheses of Post-Iboga Alkaloids

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. 1Introduction 1.1Iboga and Post-Iboga Alkaloids 1.2Classification of Post-Iboga Alkaloids 1.2.1Introduction to Type I Post-Iboga Alkaloids 1.2.2Introduction to Type II Post-Iboga Alkaloids 1.2.3Introduction to Type III Post-Iboga Alkaloids 1.2.4Introduction to Type IV Post-Iboga Alkaloids 1.2.5Introduction to Type V Post-Iboga Alkaloids 2Syntheses of Post-Iboga Alkaloids 2.1Syntheses of Type I Post-Iboga Alkaloids 2.1.1Syntheses of Monomeric Type I Post-Iboga Alkaloids 2.1.2Syntheses of Dimeric Type I Post-Iboga Alkaloids 2.2Syntheses of Type II Post-Iboga Alkaloids 2.3Synthetic Studies Toward Type III Post-Iboga Alkaloids 2.4Syntheses of Type IV Post-Iboga Alkaloids 2.5Synthesis of Type V Post-Iboga Alkaloids 3Conclusion and Outlook