Synthesis 2019; 51(14): 2737-2758
DOI: 10.1055/s-0037-1612061
review
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Post-Iboga Alkaloids

Hyeonggeun Lim
a  Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, South Korea
b  Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, South Korea   Email: sunkyu.han@kaist.ac.kr
,
Sikwang Seong
a  Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, South Korea
b  Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, South Korea   Email: sunkyu.han@kaist.ac.kr
,
Sunkyu Han*
a  Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, South Korea
b  Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, South Korea   Email: sunkyu.han@kaist.ac.kr
› Author Affiliations
This work was supported by the National Research Foundation of Korea with a grant funded by the Korean government (MSIT) (2018R1A2B6004479).
Further Information

Publication History

Received: 11 November 2018

Accepted: 18 December 2018

Publication Date:
19 February 2019 (eFirst)

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

 
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