Application and Scope of Schreiber's Gold(I)‐Catalyzed α‐Pyrone Synthesis to Ring A Aromatic Podolactones

Sanchez‐Larios, Eduardo; Giacometti, Robert D.; Hanessian, Stephen

doi:10.1002/ejoc.201402803

Cited by 12 publications

(10 citation statements)

References 35 publications

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“…Tautomerisation and proto-deauration afforded the desired α-pyrones 54 in moderate to excellent yields. Schreiber's method as well as related gold-catalysed syntheses of α-pyrones have been applied towards the total syntheses of natural products including the podolactones, [37] (+)violapyrone C [38] and neurymenolide A. [39] Fustero et al recently used a gold-catalysed ATC process for the synthesis of dihydropyridinones 57 (Scheme 13).…”

Section: -Membered Heterocyclesmentioning

confidence: 99%

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Camp

2016

Eur J Org Chem

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Auto‐tandem catalysis (ATC) is a powerful method for the synthesis of heterocycles and carbocycles as well as acyclic compounds. The process is defined as a single reagent catalysing multiple, mechanistically distinct processes of a chemical reaction. In this review recent advances in ATC using transition metal catalysts is described. In particular, the use of different catalytic systems for the controlled synthesis of the desired product, enantioselective synthesises in which multiple bonds are formed and mechanistic investigations are illustrated with applications to the synthesis of heterocycles and carbocycles as well as acyclic compounds. New approaches that use earth abundant catalysts, greener solvents or increased catalyst efficiency are highlighted. Examples of ATC reaction development are also included. In addition, ATC processes are used as key steps in the synthesis of natural products as well as biologically active compounds.

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Section: -Membered Heterocyclesmentioning

confidence: 99%

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Camp

2016

Eur J Org Chem

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“…The reactivity of intermediate 492 was further studied and extended by Hanessian and coworkers who capitalized on this α-pyrone formation for the synthesis of an aromatic congener of Urbalactone (Scheme 113, part B). 202 Scheme 110. Enamines are generally formed in situ, as shown in a synthesis of quinolines described by Arcadi and coworkers (Scheme 114).…”

Section: Alkynyl Carbonyl Derivativesmentioning

confidence: 99%

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

et al. 2020

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This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon π-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon π-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon π-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon π-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.

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“…Moreover, Schreiber's strategy has also been adapted for the total synthesis of a ring A aromatic congener of urbalactone 83. [36] In addition to their earlier work, Schreiber and co-workers investigated the synthesis of di-substituted pyrones 87 directly from propiolic acids 84 and terminal alkynes 85 via a cascade reaction based on alkyne coupling and subsequent 6-endo cyclization of intermediate 86 (Scheme 17). [37] Several functional groups like ester, halide and alkynes are compatible with the reaction conditions.…”

Section: Transition-metal-catalyzed Synthesismentioning

confidence: 99%

“…Gold-catalyzed cascade process for the conversion of propargyl propiolates 78. [35,36] Scheme 17. Synthesis of di-substituted 2-pyrones 87 from propiolic acids 84.…”

Section: Transition-metal-catalyzed Synthesismentioning

confidence: 99%

2‐Pyrone – A Privileged Heterocycle and Widespread Motif in Nature

et al. 2021

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In memory of Klaus HafnerThe 2-pyrone moiety can be found in a large number of natural products with a wide range of biological activities, including antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic, antiinflammatory and cardiotonic effects. With its heterocyclic structure encompassing the chemical nature of conjugated dienes, lactones, Michael acceptors and arenes, it can undergo a great variety of transformations such as cycloadditions, ringopening reactions, cross-couplings and lactamizations. Thus, 2-pyrones represent valuable synthetic precursors and worthwhile targets in organic, polymer, and medical chemistry. Owing to its exquisite chemical and physical properties, the synthesis and further transformations of 2-pyrones have attracted considerable attention over the past decade, showcasing transition metal and metal free strategies and using readily available starting materials, notably those stemming from renewable resources.

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Application and Scope of Schreiber's Gold(I)‐Catalyzed α‐Pyrone Synthesis to Ring A Aromatic Podolactones

Cited by 12 publications

References 35 publications

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

2‐Pyrone – A Privileged Heterocycle and Widespread Motif in Nature

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