Details
| Original language | English |
|---|---|
| Article number | ss-2021-r0249-st |
| Pages (from-to) | 975-998 |
| Number of pages | 24 |
| Journal | Synthesis (Germany) |
| Volume | 54 |
| Issue number | 4 |
| Early online date | 21 Jun 2021 |
| Publication status | Published - Feb 2022 |
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.
Keywords
- cycloaddition, Diels-Alder reaction, natural products, recent advances, stereocontrol, total synthesis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Synthesis (Germany), Vol. 54, No. 4, ss-2021-r0249-st, 02.2022, p. 975-998.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Recent Applications of the Diels-Alder Reaction in the Synthesis of Natural Products (2017-2020)
AU - Sara, Alexandru A.
AU - Um-E-Farwa, Um E.Farwa
AU - Saeed, Aamer
AU - Kalesse, Markus
N1 - Funding Information: A.S. gratefully acknowledges a postdoctoral fellowship from the Alexander von Humboldt Foundation, Germany.AlexandervonHumboldtFoundaion
PY - 2022/2
Y1 - 2022/2
N2 - 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.
AB - 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.
KW - cycloaddition
KW - Diels-Alder reaction
KW - natural products
KW - recent advances
KW - stereocontrol
KW - total synthesis
UR - http://www.scopus.com/inward/record.url?scp=85112214577&partnerID=8YFLogxK
U2 - 10.1055/a-1532-4763
DO - 10.1055/a-1532-4763
M3 - Article
AN - SCOPUS:85112214577
VL - 54
SP - 975
EP - 998
JO - Synthesis (Germany)
JF - Synthesis (Germany)
SN - 0039-7881
IS - 4
M1 - ss-2021-r0249-st
ER -