Synthesis of Novel Antitumor Agent 1-Methoxy-5,10- dioxo-5,10-dihydro-1<i>H</i>-benzo[<i>g</i>]isochromene Carboxylic Acid (3-Dimethylylaminopropyl)amide with a Dual Role Pd(II) Catalyst

Mondal, Somnath; Nogami, Tsutomu; Asao, Naoki; Yamamoto, Yoshinori

doi:10.1021/jo035016x

Cited by 94 publications

(27 citation statements)

References 24 publications

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“…auto-tandem catalysis involving the dual action of Pd II can be applied for the synthesis of an antitumor agent. [31] The same group also reported the Au-catalyzed domino hetero enyne metathesis and Nazarov cyclization (Scheme 18). [32] They proposed that the hetero enyne metatheis of 47 into 48 proceeds via the formation of a p-complex from the alkyne moiety with the cationic Au III catalyst.…”

Section: Domino Acid-acid-catalyzed Reactions In Auto-tandem Catalysismentioning

confidence: 99%

Auto‐Tandem Catalysis: A Single Catalyst Activating Mechanistically Distinct Reactions in a Single Reactor

Shindo

Takemoto

Takasu

2009

Chemistry A European J

256

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Domino reactions have received great attention as efficient synthetic methodologies for the construction of structurally complex molecules from simple materials in a single operation. Catalysts in domino reactions have also been well studied. In these reactions, a catalyst activates the substrate(s) only once, and the structure of the product is delineated at that time. Recently, the new concept of "tandem catalysis" in domino reactions, in which catalyst(s) sequentially activate more than two mechanistically distinct reactions, has been proposed. Tandem catalysis is categorized into three subclasses: orthogonal-, auto-, and assisted-tandem catalyses. Auto-tandem catalysis is defined as a process in which one catalyst promotes more than two fundamentally different reactions in a single reactor. An overview of recent and significant achievements in auto-tandem catalysis is presented in this paper.

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Section: Domino Acid-acid-catalyzed Reactions In Auto-tandem Catalysismentioning

confidence: 99%

Auto‐Tandem Catalysis: A Single Catalyst Activating Mechanistically Distinct Reactions in a Single Reactor

Shindo

Takemoto

Takasu

2009

Chemistry A European J

256

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“…[Pd(OAc) 2 ] further interacts with the alkynyl moiety of 44 and activates the intramolecular nucleophilic addition to give alkenyl ethers 45 and 46 in 5‐ exo ‐dig and 6‐ endo ‐dig cyclization modes, respectively. The auto‐tandem catalysis involving the dual action of Pd II can be applied for the synthesis of an antitumor agent 31. The same group also reported the Au‐catalyzed domino hetero enyne metathesis and Nazarov cyclization (Scheme ) 32.…”

Section: Domino Acid–acid‐catalyzed Reactions In Auto‐tandem Catalysismentioning

confidence: 99%

Glyco‐pseudopolyrotaxanes: Carbohydrate Wheels Threaded on a Polymer String and Their Inhibition of Bacterial Adhesion

Kim

Ahn

Park

et al. 2010

Chemistry A European J

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We report glyco-pseudopolyrotaxanes composed of cucurbit[6]uril-based mannose wheels (ManCB[6]) threaded on polyviologen (PV), which not only effectively induce bacterial aggregation, but also exhibit high inhibitory activity against bacterial binding to host cells. Three glyco-pseudopolyrotaxanes (1-3), which have 10, 5, and 3 ManCB[6] wheels, respectively, on a PV string, were prepared and characterized. Bacterial aggregation assays and hemagglutination inhibition assays illustrated the specific and multivalent interaction between the glyco-pseudopolyrotaxanes and E. coli ORN178. Compound 3 was especially effective at inducing bacterial aggregation and showed 300 times higher inhibitory potency than monomeric methyl-α-mannoside (Me-αMan) for ORN178-induced hemagglutination. Furthermore, we demonstrated their inhibitory activities for the adhesion of ORN178 bacteria to urinary epithelial cells as a model of urinary tract infection. Our findings suggest that these supramolecular carbohydrate clusters are potentially useful in antiadhesion therapy.

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“…Similar strategies have been employed for the synthesis of oxygen heterocycles [4b,92]. In recent studies, Yamamoto has described a method for the Pd(OAc) 2 -catalyzed conversion of 2-alkynyl benzaldehydes to isochromene derivatives (eq 62) [93], and Gabriele has demonstrated that cyclizations of 2-alkynylbenzyl alcohols selectively undergo 5-exo cyclization in methanol whereas use of dioxane as solvent favors 6-endo cyclization (eq 63) [94].…”

Section: Heterocycle Synthesis Via Hydroamination/hydroalkoxylation Rmentioning

confidence: 99%

Recent Developments in Palladium-Catalyzed Heterocycle Synthesis and Functionalization

Wolfe¹,

Thomas²

2005

COC

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Synthesis of Novel Antitumor Agent 1-Methoxy-5,10- dioxo-5,10-dihydro-1H-benzo[g]isochromene Carboxylic Acid (3-Dimethylylaminopropyl)amide with a Dual Role Pd(II) Catalyst

Cited by 94 publications

References 24 publications

Auto‐Tandem Catalysis: A Single Catalyst Activating Mechanistically Distinct Reactions in a Single Reactor

Auto‐Tandem Catalysis: A Single Catalyst Activating Mechanistically Distinct Reactions in a Single Reactor

Glyco‐pseudopolyrotaxanes: Carbohydrate Wheels Threaded on a Polymer String and Their Inhibition of Bacterial Adhesion

Recent Developments in Palladium-Catalyzed Heterocycle Synthesis and Functionalization

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