Advances in the Semi-Synthesis of Triterpenoids

Abstract

Recent achievements in triterpenoid semi-synthesis are discussed in this short review, which is divided into three parts according to the type of synthetic strategy being employed. These strategies include functionalization, modification of the carbon skeleton, and glycosylation. In the section on functionalization strategies, both functional group interconversions and new functional group installations on triterpenoid starting materials are described. The section on modification of the carbon skeleton is divided into three parts according to the tactic being applied, and incorporates rearrangement of the carbon skeleton, ring scission, and introduction of an additional heterocyclic ring. Meanwhile, in the section on glycosylation, notable achievements in the semi-synthesis of both natural and artificial triterpene saponins are discussed. Overall, the pivotal transformations that have brought about striking chemical structure variations of triterpenoid starting materials are highlighted herein, and it is hoped that this short review will provide inspiration to both established and new investigators engaged in this field of research.

1 Introduction

2 Semi-Synthesis of Triterpenoids via Functionalization Strategies

2.1 Functionalization of Rings with Functional Groups

2.2 Functionalization of a Side Chain

2.3 Functionalization of Rings without Existing Functional Groups

2.4 Functionalization of Angular Methyl Groups

2.5 Functionalization of Angular Methyl Groups and Functional-Group-Free Rings

2.6 Multisite Modifications

3 Semi-Synthesis of Triterpenoids via C-Skeleton Modification Strategies

3.1 Rearrangement Tactics

3.2 Ring-Opening Tactics

3.3 Additional Ring Introduction Tactics

4 emi-Synthesis of Triterpenoids via a Glycosylation Strategy

5 Conclusions and Outlook

Key words

triterpenoids - semi-synthesis - functionalization - C-skeleton modification - glycosylation

Publication History

Received: 12 April 2021

Accepted after revision: 05 July 2021

Accepted Manuscript online:
05 July 2021

Article published online:
11 August 2021

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