Synthesis of Raputimonoindoles A–C and Congeners

Kock, Mario; Fresia, Marvin; Jones, Peter G.; Lindel, Thomas

doi:10.1002/ejoc.201900583

Cited by 8 publications

(4 citation statements)

References 36 publications

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“…Despite formidable advances, asymmetric variants of these processes are rare. The most reliable methods depend on pre-generation of chiral 2-(pseudo)halo-1,6-dienes, which undergo diastereoselective cyclization to afford chiral cyclic derivatives . There are also a few reports demonstrating the stereoselective cyclization of olefinic organolithium compounds by using stoichiometric amounts of chiral ligands .…”

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confidence: 99%

Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction

et al. 2021

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Catalytic asymmetric dicarbofunctionalization of tethered alkenes has emerged as a promising tool for producing chiral cyclic molecules; however, it typically relies on aryl-tethered alkenes to form benzene-fused compounds. Herein, we report an enantioselective cross-electrophile divinylation reaction of nonaromatic substrates, 2-bromo-1,6-dienes. The approach thus offers a route to new chiral cyclic architectures, which are key structural motifs found in various biologically active compounds. The reaction proceeds under mild conditions, and the use of chiral t-Bu-pmrox and 3,5-difluoro-pyrox ligands resulted in the formation of divinylated products with high chemo-, regio-, and enantioselectivity. The method is applicable for the incorporation of chiral hetero-and carbocycles into complex molecules.

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confidence: 99%

Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction

et al. 2021

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“…Remarkably, the total synthesis of raputimonoindole congeners 143 and 147 , both having indole skeletons was effected in the laboratory of Lindel's group with the involvement of RCM reaction at the later‐stage of their synthesis (Scheme 6). [182] In this study, etherification of an allylic alcohol 141 with 3‐bromo‐2‐methylpropane using NaH resulted a diene 142 , which upon RCM in the presence of G‐II catalyst followed by the removal of SEM‐group furnished 143 in 86% yield. Whileas, esterification of an allylic alcohol 144 with methacrylic anahydride using pyridine base generated an α , β ‐unsaturated lactone 145 , which on RCM reaction with G‐II/Ti(O i Pr) 4 furnished a lactone 146 in a significant yield.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 77%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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“…In 2019, Lindel and co-workers reported a concise total synthesis of raputimonoindoles A-C, indole alkaloids isolated from the bark and roots of Amazonian tree Raputia simulans (Scheme 14). [39] In their approach, raputimonoindole B was afforded directly by Ir-catalyzed CÀ H borylation followed by Pdcatalyzed Suzuki-Miyaura cross-coupling of 3-carbometh- oxyfuran. The selective CÀ H borylation enables the formation of C5 pinacol boronate ester in high yield by sterically-directed CÀ H borylation.…”

Section: Non-photoredox Cà H Functionalizationmentioning

confidence: 99%

Synthesis of Natural Products by C−H Functionalization of Heterocycless

Yang

Szostak

2022

Chemistry A European J

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Total synthesis is considered by many as the finest combination of art and science. During the last decades, several concepts were proposed for achieving the perfect vision of total synthesis, such as atom economy, step economy, or redox economy. In this context, C−H functionalization represents the most powerful platform that has emerged in the last years, empowering rapid synthesis of complex natural products and enabling diversification of bioactive scaffolds based on natural product architectures. In this review, we present an overview of the recent strategies towards the total synthesis of heterocyclic natural products enabled by C−H functionalization. Heterocycles represent the most common motifs in drug discovery and marketed drugs. The implementation of C−H functionalization of heterocycles enables novel tactics in the construction of core architectures, but also changes the logic design of retrosynthetic strategies and permits access to natural product scaffolds with novel and enhanced biological activities.

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Synthesis of Raputimonoindoles A–C and Congeners

Cited by 8 publications

References 36 publications

Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction

Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Synthesis of Natural Products by C−H Functionalization of Heterocycless

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