Use of Transition Metal–catalyzed Cascade Reactions in Natural Product Synthesis and Drug Discovery

Xu, Pengfei; Wei, Hao

doi:10.1002/9781118356654.ch7

Cited by 7 publications

(3 citation statements)

References 175 publications

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“…In recent years chemists have tried to emulate Nature by the development of one-pot asymmetric multicatalytic reactions to construct enantiomerically enriched molecules, also fulfilling important green chemistry principles related to the minimization of waste production and time-consuming and tedious purification steps associated with traditional multistep processes . In particular, two different catalytic worlds (metal catalysis and biocatalysis) have recently converged in the development of new methodologies merging the advantages of both areas . However, this assembly has been mainly reported in volatile organic compounds (VOCs) as solvents (e.g., dynamic kinetic resolutions (DKRs) by combining a racemizing metal catalyst with a biotransformation) .…”

Section: Introductionmentioning

confidence: 99%

Combination of Metal-Catalyzed Cycloisomerizations and Biocatalysis in Aqueous Media: Asymmetric Construction of Chiral Alcohols, Lactones, and γ-Hydroxy-Carbonyl Compounds

et al. 2017

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The combination of the metal-catalyzed cycloisomerization of alkynes containing a tethered nucleophile as substituent in aqueous media (followed by the spontaneous hydrolysis, hydroalkoxylation, or aminolysis of the transiently formed five-membered heterocycles) with the subsequent enantioselective ketone bioreduction (mediated by KREDs) has been achieved. The overall transformations, which formally involve a three-step one-pot reaction, provide a variety of enantiopure valuable molecules (e.g., 1,4-diols, lactones, and γ-hydroxy-carbonyl compounds (carboxylic acids, esters, and amides)) with high conversions and enantioselectivities and under mild reaction conditions, disclosing the concept of integrated metal-catalyzed cycloisomerizations of alkynes and enzymatic catalysis in water.

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Section: Introductionmentioning

confidence: 99%

Combination of Metal-Catalyzed Cycloisomerizations and Biocatalysis in Aqueous Media: Asymmetric Construction of Chiral Alcohols, Lactones, and γ-Hydroxy-Carbonyl Compounds

et al. 2017

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“…Over the past decade, the domino or cascade reaction has become a powerful and ingenious strategy for the synthesis of natural products or complex compounds . It has shown undeniable advantages, including extensive functional group compatibility and the economies of labor and cost.…”

mentioning

confidence: 99%

Diphenyl-Diselenide-Mediated Domino Claisen-Type Rearrangement/Cyclization of Propargylic Aryl Ethers: Synthesis of Naphthofuran-2-carboxaldehyde Derivatives

et al. 2019

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A diphenyl-diselenide-mediated Claisen-type rearrangement/cyclization of propargylic aryl ethers under metal-free conditions is developed, affording various naphthofuran-2-carboxaldehydes in moderate to excellent yield. The broad substrate scope and excellent functional group compatibility suggest that it can be a straightforward and powerful method to access naphthofuran-2-carboxaldehydes in a highly regioselective manner. Moreover, this reaction can be scaled up to the gram scale.

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“…The development of novel domino, tandem, or cascade processes catalyzed by cheap and abundant first-row transition metals, especially involving unstable intermediates, has the potential to provide practical, atom- and step-economic access to complex structures. In sharp contrast to large amounts of reports on the Claisen rearrangements of noncumulated double bonds, examples of Claisen rearrangements of allenes are very limited and underdeveloped .…”

mentioning

confidence: 99%

Iron(III)-Catalyzed Domino Claisen Rearrangement/Regio- and Chemoselective Aerobic Dehydrogenative Cyclization of β-Naphthyl-Substituted-Allenylmethyl Ether

Zhang

Zhi

et al. 2019

Org. Lett.

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An FeCl3-catalyzed allenic Claisen rearrangement/regio- and chemoselective aerobic dehydrogenative cyclization domino reaction is developed, providing a wide range of 2-aryl/alkyl, 3-(substituted-vinyl)naphtho[2,1-b]furans in high yields at 95–130 °C in an atom- and step-economic fashion. Mechanistic studies suggest that the FeCl3 catalyst is responsible for the high regio- and chemoselectivity in reaction. A blue-emitting product shows quantum yield of 0.95. The reaction proceeds readily on the gram scale, and synthetic applications of the products are also demonstrated.

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Use of Transition Metal–catalyzed Cascade Reactions in Natural Product Synthesis and Drug Discovery

Cited by 7 publications

References 175 publications

Combination of Metal-Catalyzed Cycloisomerizations and Biocatalysis in Aqueous Media: Asymmetric Construction of Chiral Alcohols, Lactones, and γ-Hydroxy-Carbonyl Compounds

Combination of Metal-Catalyzed Cycloisomerizations and Biocatalysis in Aqueous Media: Asymmetric Construction of Chiral Alcohols, Lactones, and γ-Hydroxy-Carbonyl Compounds

Diphenyl-Diselenide-Mediated Domino Claisen-Type Rearrangement/Cyclization of Propargylic Aryl Ethers: Synthesis of Naphthofuran-2-carboxaldehyde Derivatives

Iron(III)-Catalyzed Domino Claisen Rearrangement/Regio- and Chemoselective Aerobic Dehydrogenative Cyclization of β-Naphthyl-Substituted-Allenylmethyl Ether

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