Total Synthesis of 3-&lt;i&gt;epi&lt;/i&gt;-Juruenolide C

Kutsumura, Noriki; Inagaki, Mai; Kiriseko, Akito; Saito, Takao

doi:10.1248/cpb.c19-00209

Cited by 4 publications

(1 citation statement)

References 42 publications

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“…Transition-metal-catalyzed carbonylative cross-coupling reactions are considered to be one of the most efficient methods for synthesizing a diverse array of carbonyl compounds. Such carbonylations are widely utilized in pharmaceutical synthesis, [1] total synthesis of natural products, [2] and valuable chemical manufacturing in industry. [3] Carbonyl group installation can be realized by employing carbon monoxide (CO), an economical one-carbon building block.…”

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confidence: 99%

Silylcarboxylic Acids as Bifunctional Reagents: Application in Palladium‐Catalyzed External‐CO‐Free Carbonylative Cross‐Coupling Reactions

Xiong

et al. 2020

Adv Synth Catal

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A palladium-catalyzed external-CO-free carbonylative Hiyama-Denmark cross-coupling reaction is presented. The introduction of silylcarboxylic acids as bifunctional reagents (CO and nucleophile source) avoids the need for external gaseous CO and a silylarene coupling partner. The transformation features high functional group tolerance and it is successful with electron-rich,-neutral, and-poor aryl iodides. Stoichiometric studies and control experiments provide insight into the reaction mechanism and support the hypothesized dual role of silylcarboxylic acids.

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mentioning

confidence: 99%

Silylcarboxylic Acids as Bifunctional Reagents: Application in Palladium‐Catalyzed External‐CO‐Free Carbonylative Cross‐Coupling Reactions

Xiong

et al. 2020

Adv Synth Catal

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CO‐Free Aminocarbonylation of Terminal Alkynes Catalyzed by Synergistic Effect From Metal–Organic Frameworks

Zhao,

Zhang,

et al. 2024

Advanced Science

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Incorporation of CO into substrates to construct high‐value carbonyl compounds is an intensive industrial carbonylation procedure, however, high toxicity and wide explosion limits (12.5–74.0 vol% in air) of CO limit its application in industrial production. The development of a CO‐free catalytic system for carbonylation is one of ideal methods, but full of challenge. Herein, this study reports the CO‐free aminocarbonylation conversion of terminal alkynes synergistically catalyzed by a unique Co(ІІ)/Ag(І) metal–organic framework (MOF), in which the combination of isocyanides and O2 is employed as safe and green source of aminocarbonyl. This reaction has broad substrate applicability in terminal alkyne and isocyanides components with 100% atom economy. The bimetal MOF catalyst can be recycled at least five times without substantial loss of catalytic activities. Mechanistic investigations demonstrate that the synergistic effect between Ag(I) and Co(II) sites can efficiently activate terminal alkyne and isocyanides, respectively. Free radical capture experiments, FT‐IR analysis and theoretical explorations further reveal that terminal alkynes and isocyanides can be catalytically transformed into an anionic intermediate through heterolysis pathways. This work provides secure and practical access to carbonylation as well as a new approach to aminocarbonylation of terminal alkynes.

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Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

Ujiie,

Tanaka,

Arai

et al. 2024

J Nat Med

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Total Synthesis of 3-<i>epi</i>-Juruenolide C

Cited by 4 publications

References 42 publications

Silylcarboxylic Acids as Bifunctional Reagents: Application in Palladium‐Catalyzed External‐CO‐Free Carbonylative Cross‐Coupling Reactions

Silylcarboxylic Acids as Bifunctional Reagents: Application in Palladium‐Catalyzed External‐CO‐Free Carbonylative Cross‐Coupling Reactions

CO‐Free Aminocarbonylation of Terminal Alkynes Catalyzed by Synergistic Effect From Metal–Organic Frameworks

Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

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