Troponoid Compounds as Therapeutic Agents and as Targets and Templates for Chemical Synthesis

Abstract

The renewed interest in troponoid compounds as potential therapeutic agents and the ongoing discovery of new, naturally occurring and biologically active members of the class has resulted in an attendant focus on developing and deploying methods for their synthesis. This account highlights some of the significant recent developments in the area of troponoid chemistry that serve to contextualize our group’s longstanding and ongoing interest in the synthesis of such compounds through the cyclopropane-mediated ring-expansion of cyclohexanoid and benzenoid compounds. The various means by which such conversions can be accomplished and their application to the synthesis of both natural and non-natural troponoids are detailed.

1 Introduction

2 Naturally Occurring Troponoid Compounds and Their Biogenesis

3 Medicinal Chemistry Aspects of Troponoid Compounds

4 Troponoids in Materials Science

5 Troponoids as Scaffolds in Chemical Synthesis

6 An Overview of the Methods Available for Preparing Troponoids

7 Cyclopropane-Mediated Ring-Expansion Reactions Leading to Troponoids

8 Conclusions

Key words

total synthesis - cycloaddition - natural products - pericyclic reaction - ring-expansion

Publication History

Received: 11 July 2022

Accepted after revision: 16 August 2022

Accepted Manuscript online:
16 August 2022

Article published online:
16 November 2022

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