Synthesis of 3,4-Fused Tricyclic Indoles through Cascade Carbopalladation and C–H Amination: Development and Total Synthesis of Rucaparib

Cheng, Cang; Zuo, Xiang; Tu, Dongdong; Wan, Bin; Zhang, Yanghui

doi:10.1021/acs.orglett.0c01513

Cited by 52 publications

(26 citation statements)

References 53 publications

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“…Cascade enzyme reactions have been utilized with different purposes, especially in the development of a more-efficient synthesis of chemical compounds, such as bioactive oligosaccharides, glycosylated molecules, or amoniacid derivatives [21][22][23][24][25][26].…”

Section: Enzymatic Cascade Processesmentioning

confidence: 99%

Recent Advances in Enzymatic and Chemoenzymatic Cascade Processes

et al. 2020

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Cascade reactions have been described as efficient and universal tools, and are of substantial interest in synthetic organic chemistry. This review article provides an overview of the novel and recent achievements in enzyme cascade processes catalyzed by multi-enzymatic or chemoenzymatic systems. The examples here selected collect the advances related to the application of the sequential use of enzymes in natural or genetically modified combination; second, the important combination of enzymes and metal complex systems, and finally we described the application of biocatalytic biohybrid systems on in situ catalytic solid-phase as a novel strategy. Examples of efficient and interesting enzymatic catalytic cascade processes in organic chemistry, in the production of important industrial products, such as the designing of novel biosensors or bio-chemocatalytic systems for medicinal chemistry application, are discussed

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Section: Enzymatic Cascade Processesmentioning

confidence: 99%

Recent Advances in Enzymatic and Chemoenzymatic Cascade Processes

et al. 2020

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“…Moreover, a range of macrocyclic 3,5-and 3,6-fused indoles can be also created, which largely expands the scaffold diversity. Shortly after this work published, two independent works (Cheng et al, 2020;Zhang et al, 2020) were reported using similar catalytic systems for synthesis of 3,4fused indoles by using N,N-di-tert-butyldiaziridinone as the Nsource. By employing this cascade cyclization, Cheng et al (2020) accomplished a concise synthesis of rucaparib, which is a PARP-1 inhibitor and a Food and Drug Administration-approved cancer medicine.…”

Section: Construction Of Polycyclic Heterocycles Fused Pyridines and mentioning

confidence: 99%

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Zheng

Hua

2020

Front. Chem.

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Polycyclic scaffolds are omnipresent in natural products and drugs, and the synthetic strategies and methods toward construction of these scaffolds are of particular importance. Compared to simple cyclic ring systems, polycyclic scaffolds have higher structure complexity and diversity, making them suitable for charting broader chemical space, yet bringing challenges for the syntheses. In this review, we surveyed progress in the past decade on synthetic methods for polycyclic natural product scaffolds, in which the key steps are one-pot reactions involving intermolecular or intramolecular alkyne annulation. Synthetic strategies of selected polycyclic carbocycles and heterocycles with at least three fused, bridged, or spiro rings are discussed with emphasis on the synthetic efficiency and product diversity. Recent examples containing newly developed synthetic concepts or toolkits such as collective and divergent total synthesis, gold catalysis, C-H functionalization, and dearomative cyclization are highlighted. Finally, several "privileged synthetic strategies" for "privileged polycyclic scaffolds" are summarized, with discussion of remained challenges and future perspectives.

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“…Almost at the same time, Zhang and co-workers reported a similar tricyclic indole synthesis by applying a comparable strategy, but using N,N-di-tert-butyldiaziridinone 49 as the amination reagent. 52…”

Section: Short Review Synthesis Scheme 28 Synthesis Of Spirocyclic Prmentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents

et al. 2020

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Transition-metal-catalyzed direct inert C–H bond functionalization has attracted much attention over the past decades. However, because of the high strain energy of the suspected palladacycle generated via C–H bond palladation, direct functionalization of a C–H bond less than a three-bond distance from a catalyst center is highly challenging. In this short review, we summarize the advances on palladium-catalyzed bridging C–H activation, in which an inert proximal C–H bond palladation is promoted by the elementary step of migratory insertion of an alkene, an alkyne or a metal carbene intermediate.1 Introduction2 Palladium-Catalyzed Alkene Bridging C–H Activation2.1 Intramolecular Reactions2.2 Intermolecular Reactions3 Palladium-Catalyzed Alkyne Bridging C–H Activation3.1 Intermolecular Reactions3.2 Intramolecular Reactions4 Palladium-Catalyzed Carbene Bridging C–H Activation5 Conclusion and Outlook

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Synthesis of 3,4-Fused Tricyclic Indoles through Cascade Carbopalladation and C–H Amination: Development and Total Synthesis of Rucaparib

Cited by 52 publications

References 53 publications

Recent Advances in Enzymatic and Chemoenzymatic Cascade Processes

Recent Advances in Enzymatic and Chemoenzymatic Cascade Processes

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents

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