Total Synthesis of (+)-Gilbertine: A Cyclopentanone-Based Approach

Wei, Bei; Peng, Cheng; Zu, Liansuo

doi:10.1021/acs.orglett.2c02778

Cited by 4 publications

(2 citation statements)

References 19 publications

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“…Distinguished from carbene-mediated multicomponent reactions (MCR), CR involves a stable and isolatable intermediate. An illustrative example is provided by Zu's group, showcasing a cascade reaction of diazoketones and aminoketones for the construction of carbazolone and indolone backbones, facilitating the asymmetric total synthesis of (+)-leucomidine A and (+)-glibertine [110,111] (Figure 17). Diazoketone 137 and aminoketone 138 go through NÀ H insertion/Aldol addition/CO migration cascade to render indolone (when R 1 = alkyl) or carbazolone (when R 1 = H) (Figure 17a).…”

Section: Cascade Reactionmentioning

confidence: 99%

Asymmetric Carbene Transfer: Enhancing Chemical Diversity for Drug Discovery

Shi,

2024

Chemistry A European J

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The exploration of chemical space for disease targets is of paramount importance. However, the current repertoire of chemically synthesized compounds, numbering around 108, merely scratches the surface in comparison to the theoretical diversity of 1060. Organic chemists are actively engaged in pioneering methodologies to expand this constrained space. Among these innovative approaches, Asymmetric Carbene Transfer (ACT) emerges as a potent strategy for enhancing molecular diversity. This article critically examines the efficacy of ACT in synthesizing pharmaceutically relevant molecules, encompassing natural products and bioactive compounds. We highlight its pivotal role in the synthesis of 25 compounds. By unraveling the diverse applications of ACT, this review illuminates its potential impact on drug discovery. Furthermore, we propose future methodology directions, contributing to the ongoing discourse within the medicinal chemistry community. In summary, this review article navigates the landscape of ACT, showcasing its prowess in expanding chemical space for drug discovery. Through a nuanced exploration of its applications and a forward‐looking approach, we contribute to the collective understanding of ACT's potential and chart a course for future advancements in ACT for drug discovery.

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Section: Cascade Reactionmentioning

confidence: 99%

Asymmetric Carbene Transfer: Enhancing Chemical Diversity for Drug Discovery

Shi,

2024

Chemistry A European J

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“…Polycyclic N-heteroaromatics (PNAs) including pyridine-fused molecules are prevalent in biologically active compounds, pharmaceuticals, and functional materials, − especially the supercapacitors , and photoelectrodes , of photoelectron-chemical cells (Scheme a). In general, multistep prefunctionalization including halogenation, condensation, addition, oxidation and final coupling, and cyclization is usually inevitable to construct the PNAs. − In contrast, the more straightforward and powerful method for building highly functionalized polycyclic aromatic compounds (PAs) was developed via a one-pot multistep cascade cyclization − or transition-metal-catalyzed annulative π-extension. − In general, attack of the radical or transition metal at the corresponding π system mediated the cascade processes to construct the desired PAs. A tin radical was usually employed as the tethered initiator and final leaving group.…”

Section: Introductionmentioning

confidence: 99%