Development of Cationic Diels-Alder Reaction in Highly Polar Media and Total Syntheses of Natural Products.

The Diels-Alder reaction has long established its high rank in the toolbox of any natural product chemist. The tremendous toleration of building blocks of various complexity and derivatization degree, as well as the enablement of furnishing six-membered rings with well-defined stereochemistry represents its main features and advantages. In recent years, many total syntheses of natural products relied 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 or domino-Diels-Alder reactions have been employed to extend the scope in the synthesis of natural products. Our review covers the application of the Diels-Alder reaction in natural product syntheses from 2017 to 2020, as well as selected methodologies which were inspired by, or could be used to access natural products.

Download Full-text

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

Current Organic Chemistry ◽

10.2174/1385272820666160331234709 ◽

2016 ◽

Vol 20 (22) ◽

pp. 2421-2442 ◽

Cited By ~ 2

Author(s):

Kévin Cottet ◽

Maria Kolympadi ◽

Dean Markovic ◽

Marie-Christine Lallemand

Keyword(s):

Natural Products ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

Download Full-text

Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review

Current Organic Synthesis ◽

10.2174/1570179414666170821120234 ◽

2018 ◽

Vol 15 (2) ◽

pp. 221-229 ◽

Cited By ~ 3

Author(s):

Shah Bakhtiar Nasir ◽

Noorsaadah Abd Rahman ◽

Chin Fei Chee

Keyword(s):

Natural Products ◽

Organic Synthesis ◽

Lewis Acid ◽

Alder Reaction ◽

Diels Alder ◽

Enantioselective Synthesis ◽

Chiral Ligand ◽

Asymmetric Syntheses ◽

Diels Alder Reaction ◽

Enantioselective Syntheses

Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

Download Full-text

Total synthesis of halogenated monoterpene marine natural products via the Diels-Alder reaction

The Journal of Organic Chemistry ◽

10.1021/jo00220a013 ◽

1985 ◽

Vol 50 (20) ◽

pp. 3738-3749 ◽

Cited By ~ 16

Author(s):

Paul G. Williard ◽

Stephen E. De Laszlo

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Marine Natural Products ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

Download Full-text

Total syntheses of ericifolione and analogues via a biomimetic inverse-electron-demand Diels-Alder reaction

Chemical Communications ◽

10.1039/d1cc06361h ◽

2021 ◽

Author(s):

Tingting Zhou ◽

Anquan Zheng ◽

Luqiong Huo ◽

Changgeng Li ◽

Haibo Tan ◽

...

Keyword(s):

Sodium Acetate ◽

Alder Reaction ◽

Diels Alder ◽

Total Syntheses ◽

Inverse Electron Demand ◽

Diels Alder Reaction ◽

Sterically Hindered ◽

Electron Demand

Driven by bioinspiration and appreciation of the structure of ericifolione, a biomimetic tautomerization/intermolecular inverse-electron-demand hetero Diels-Alder reaction cascade sequence promoted by sodium acetate to rapidly construct sterically hindered dihydropyran scaffolds...

Download Full-text