Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

Alexandru A. Sara; Um-e-Farwa Um-e-Farwa; Aamer Saeed; Markus Kalesse

doi:10.1055/a-1532-4763

Synthesis 2022; 54(04): 975-998
DOI: 10.1055/a-1532-4763

special topic

Cycloadditions – Established and Novel Trends – in Celebration of the 70th Anniversary of the Nobel Prize Awarded to Otto Diels and Kurt Alder

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

Alexandru A. Sara‡

^aLeibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1 B, 30167 Hannover, Germany

,

Um-e-Farwa Um-e-Farwa‡

^bQuaid-I-Azam University, Department of Chemistry, Islamabad-45320, Pakistan

,

Aamer Saeed ∗

^bQuaid-I-Azam University, Department of Chemistry, Islamabad-45320, Pakistan

,

Markus Kalesse ∗

^aLeibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1 B, 30167 Hannover, Germany

^cHelmholtz Zentrum für Infektionsforschung (HZI), Inhoffenstraße 7, 38124 Braunschweig, Germany

› Author Affiliations

Abstract

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Abstract

The Diels–Alder reaction has long been established as an extremely useful procedure in the toolbox of natural product chemists. It tolerates a wide spectrum of building blocks of different complexity and degrees of derivatization, and enables the formation of six-membered rings with well-defined stereochemistry. In recent years, many total syntheses of natural products have been reported that rely, at some point, on the use of a [4+2]-cycloaddition step. Among classic approaches, several modifications of the Diels–Alder reaction, such as hetero-Diels–Alder reactions, dehydro-Diels–Alder reactions and domino-Diels–Alder reactions, have been employed to extend the scope of this process in the synthesis of natural products. Our short review covers applications of the Diels–Alder reaction in natural product syntheses between 2017 and 2020, as well as selected methodologies which are inspired by, or that can be used to access natural products.

1 Introduction

2 Syntheses from 2017

3 Syntheses from 2018

4 Syntheses from 2019

5 Syntheses from 2020

6 Conclusion

Key words

Diels–Alder reaction - cycloaddition - total synthesis - natural products - recent advances - stereocontrol

Full Text

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