Enantioselective Syntheses of Yohimbine Alkaloids: Proving Grounds for New Catalytic Transformations

Abstract

The total synthesis of bioactive alkaloids is an enduring challenge and an indication of the state of the art of chemical synthesis. With the explosion of catalytic asymmetric methods over the past three decades, these compelling targets have been fertile proving grounds for enantioselective bond forming transformations. These activities are summarized herein both to highlight the power and versatility of these methods and to instill future inspiration for new syntheses of these privileged natural products.

1 Introduction

2 Monoterpenoid Indole Alkaloids

2.1 Corynanthe-Type MIAs

3 Biosynthesis

4 Biological Activity

5 Scope

6 Strategies in Yohimbine Alkaloid Synthesis

6.1 Momose’s Formal Synthesis of (+)-Yohimbine

6.2 Jacobsen’s Synthesis of (+)-Yohimbine

6.3 Hiemstra’s Synthesis of (+)-Yohimbine

6.4 Qin’s Synthesis of (–)-Yohimbine

6.5 Tan’s Synthesis of (+)-Rauwolscine

6.6 Jacobsen’s Synthesis of (+)-Reserpine

6.7 Chen’s Synthesis of (+)-Reserpine

6.8 Riva’s Synthesis of (–)-Alloyohimbane

6.9 Katsuki’s Synthesis of (–)-Alloyohimbane

6.10 Ghosh’s Synthesis of (–)-Yohimbane and (–)-Alloyohimbane

6.11 Hong’s Synthesis of (–)-Yohimbane

6.12 Gellman’s Synthesis of (–)-Yohimbane

6.13 Scheidt’s Synthesis of (–)-Rauwolscine and (–)-Alloyohimbane

7 Conclusion

Key words

asymmetric synthesis - asymmetric catalysis - alkaloids - total synthesis - catalysis

Publication History

Received: 21 September 2021

Accepted after revision: 02 November 2021

Accepted Manuscript online:
02 November 2021

Article published online:
04 January 2022

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