ChemInform Abstract: Recent Advances of Intermolecular Diels-Alder Reaction in Bio-Inspired Synthesis of Natural Products

Recent advances and examples of the intramolecular Diels–Alder reaction are summarized and applications to the total synthesis of natural products, both completed and in progress, noted. A detailed discussion of trienes leading to bicyclo[4.3.0]nonene skeletons is followed by examples of bicyclo[4.4.0]decenes and adducts arising from ortho-quinodimethane precursors. Cycloadditions affording bicyclo[n.4.0] systems and bridged-ring adducts from cyclic dienes conclude this survey which is followed by a discussion of unreactive trienes and a brief analysis of synthetic strategy to complete the review.

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Recent advances of intermolecular Diels-Alder reaction in bio-inspired synthesis of natural products

Science China Chemistry ◽

10.1007/s11426-014-5144-5 ◽

2014 ◽

Vol 57 (7) ◽

pp. 926-929 ◽

Cited By ~ 21

Author(s):

ChunYun Wan ◽

Jun Deng ◽

Hua Liu ◽

Ming Bian ◽

Ang Li

Keyword(s):

Natural Products ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Recent Advances

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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

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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.

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