Progress toward the Synthesis of the Basiliolides and Transtaganolides:  An Intramolecular Pyrone Diels−Alder Entry into a Novel Class of Natural Products

2008 ◽  
Vol 10 (1) ◽  
pp. 25-28 ◽  
Author(s):  
Hosea M. Nelson ◽  
Brian M. Stoltz
Keyword(s):  
Natural Products ◽  
Diels Alder

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

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

2018 ◽  
Vol 15 (2) ◽  
pp. 221-229 ◽  
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.

Intramolecular Diels–Alder Reactions of Oxazoles, Imidazoles, and Thiazoles

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Wipf ◽  
Thanh T. Nguyen
Keyword(s):  
Natural Products ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Copper Catalysts ◽  
Diels Alder ◽  
Synthetic Approach ◽  
Highly Efficient ◽  
Intramolecular Cycloadditions ◽  
Western Segment ◽  
Target Molecules

AbstractThe development of the intramolecular Diels–Alder cycloaddition­ of azole heterocycles, i.e. oxazoles (IMDAO), imidazoles (IMDAI), and thiazoles (IMDAT), has had a significant impact on the efficient preparation of heterocyclic intermediates and natural products. In particular, highly efficient and versatile IMDAO reactions have been utilized as a key step in several synthetic schemes to provide alkaloids and terpenoid target molecules. More limited studies have been performed on IMDAI and IMDAT cycloadditions. Some drawbacks, such as the occasionally­ challenging preparation of IMDA precursors, are also highlighted in this review. Perspectives are provided on how IMDAI and IMDAT­ transformations can be further expanded for target-directed syntheses.1 Introduction2 Oxazoles2.1 IMDAO Approaches to Furanosesquiterpenes and Furanosteroids2.1.1 Syntheses of Highly Oxygenated Sesquiterpenes2.1.2 Syntheses of (±)-Gnididione and (±)-Isognididione2.1.3 Synthesis of (±)-Stemoamide2.1.4 Synthesis of (±)-Paniculide A2.1.5 Syntheses of (+)- and (–)-Norsecurinine2.1.6 Synthesis of Evodone2.1.7 Syntheses of (±)-Ligularone and (±)-Petasalbine2.1.8 Syntheses of Imerubrine, Isoimerubrine, and Grandirubrine2.1.9 Syntheses of Furanosteroids2.1.10 Syntheses of Substituted Indolines and Tetrahydroquinolines2.2 IMDAO Approaches to Pyridines: the Kondrat’eva Reaction2.2.1 Syntheses of Suaveoline and Norsuaveoline2.2.2 Synthesis of Eupolauramine2.2.3 Syntheses of (–)-Plectrodorine and (+)-Oxerine2.2.4 Synthesis of Amphimedine2.2.5 Synthetic Approach to the Western Segment of Haplophytine2.2.6 Synthesis of Marinoquinoline A2.2.6.1 IMDAO Approach to Marinoquinoline A2.2.6.2 Scope of Allenyl IMDAO Cycloaddition2.3 Lewis Acid Catalysis in IMDAO Reactions2.3.1 Effects of Europium Catalysts on IMDAO Reactions2.3.2 Effects of Copper Catalysts on IMDAO Reactions3 Imidazoles 4 Thiazoles4.1 Syntheses of Menthane and Eremophilane4.2 Further Comments on the Intramolecular Cycloadditions of Thiocarbonyl Ylides5 Conclusions and Outlook

Microwave-Assisted Claisen Rearrangement/Diels–Alder Cascade reaction for the Synthesis of Caged Garcinia Natural Products and Analogues

2011 ◽  
Vol 35 (11) ◽  
pp. 630-633 ◽  
Author(s):  
Xiang Li ◽  
Xiaojin Zhang ◽  
Zhuoqin Yu ◽  
Xiaorong Liu ◽  
Qidong You ◽  
...  
Keyword(s):  
Natural Products ◽  
Claisen Rearrangement ◽  
Cascade Reaction ◽  
Diels Alder ◽  
Microwave Assisted

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

1985 ◽  
Vol 50 (20) ◽  
pp. 3738-3749 ◽  
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

Involvement of Diels–Alder reactions in the biosynthesis of secondary natural products: the late stage of the biosynthesis of the phytotoxins solanapyrones

1999 ◽  
pp. 1225 ◽  
Author(s):  
Hideaki Oikawa ◽  
Yuichi Suzuki ◽  
Kinya Katayama ◽  
Akira Naya ◽  
Chiaki Sakano ◽  
...  
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Diels Alder ◽  
Secondary Natural Products

Catalytic enantioselective diels-alder addition to furan provides a direct synthetic route to many chiral natural products

1993 ◽  
Vol 34 (25) ◽  
pp. 3979-3982 ◽  
Author(s):  
E.J. Corey ◽  
Teck-Peng Loh
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Synthetic Route
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