Synthetic Strategies to Access Heteroatomic Spirocentres Embedded in Natural Products

Michael P. Badart; Bill C. Hawkins

doi:10.1055/a-1379-2312

Synthesis, Table of Contents

Synthesis 2021; 53(10): 1683-1705
DOI: 10.1055/a-1379-2312

review

Synthetic Strategies to Access Heteroatomic Spirocentres Embedded in Natural Products

Michael P. Badart∗

,

Bill C. Hawkins∗

Abstract

All articles of this category

Abstract

The spirocyclic motif is abundant in natural products and provides an ideal three-dimensional template to interact with biological targets. With significant attention historically expended on the synthesis of flat-heterocyclic compound libraries, methods to access the less-explored three-dimensional medicinal-chemical space will continue to increase in demand. Herein, we highlight by reaction class the common strategies used to construct the spirocyclic centres embedded in a series of well-studied natural products.

1 Introduction

2 Cycloadditions

3 Palladium-Catalysed Coupling Reactions

4 Conjugate Additions

5 Imines, Aminals, and Hemiaminal Ethers

6 Mannich-Type Reactions

7 Oxidative Dearomatisation

8 Alkylation

9 Organometallic Additions

10 Conclusions

Key words

spiro compounds - total synthesis - cycloaddition - Michael addition - palladium - natural products

Full Text

References

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