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
M.P.B. gratefully acknowledges the University of Otago for the provision of a Ph.D. scholarship.


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



Publication History

Received: 15 December 2020

Accepted after revision: 01 February 2021

Publication Date:
01 February 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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