Enantioselective Total Syntheses of Lyconadins A–E through a Palladium‐Catalyzed Heck‐Type Reaction

Zhang, Jiayang; Yan, Yang-Tian; Hu, Rong; Li, Ting; Bai, Wen‐Ju; Yang, Yang

doi:10.1002/ange.201912948

Cited by 9 publications

(1 citation statement)

References 71 publications

(38 reference statements)

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“…Although palladium is a valuable metal due to its scarcity, it is widely used to get almost everywhere. − It is an essential part for catalytic converters in the automobiles . It is applied in the coupling reactions such as Heck, , Sonogashira, and Suzuki–Miyaura for the production of pharmaceuticals, fine chemicals, plastics, and high-tech materials in both industry and extensive research in academia. However, Pd-catalyzed reactions often generate products with Pd residue contamination even after purification.…”

Section: Introductionmentioning

confidence: 99%

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Mosleh,

Hardaker,

Bartolini

et al. 2024

ACS Appl. Opt. Mater.

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Due to vast application of palladium in academia and industry and its toxicity, it is critical to develop user-friendly, portable, and affordable methods for accurately detecting ultratrace Pd. In this study, a highly sensitive and selective fluorescent probe (N-butyl-4-alloxy-1,8-naphthalimide, compound 2) was synthesized, which demonstrated multiple signals [enhanced fluorescence (FL), ratiometric FL, and colorimetric responses] upon interaction with palladium. The compound 2 was designed by incorporating a naphthalimidebased fluorescent dye as the fluorophore and an allyl ether group as a responsive unit. Utilizing a Pd 0 -triggered cleavage reaction by a deallylation reaction through the Tsuji−Trost reaction, compound 2 exhibited rapid response, wide linearity, exceptional sensitivity with a limit of detection as low as 2.2 pM, and high selectivity toward palladium species. In addition, as a ratiometric and enhanced FL response, the probe could be developed as a portable sensor via naked eye visualization for semiquantitative and selective detection of palladium. Integrating with an easily available smartphone (with a camera and a color-analysis app), potential in situ quantitative detection was achieved at a low cost. The probe shows multiple signals for palladium detection and potential as a portable sensor, and this work provides valuable insights into developing sensors with good sensitivity, selectivity, improved reliability, and portability for detection of palladium and other analytes of interest.

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Section: Introductionmentioning

confidence: 99%

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Mosleh,

Hardaker,

Bartolini

et al. 2024

ACS Appl. Opt. Mater.

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A Divergent Enantioselective Total Synthesis of Post‐Iboga Indole Alkaloids

2020

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Divergent enantioselective total syntheses of five naturally occurring post-iboga indole alkaloids,d ippinine B and C, 10,11-demethoxychippiine,3-O-methyl-10,11-demethoxychippiine,a nd 3-hydroxy-3,4-secocoronaridine,a sw ell as the two analogues 11-demethoxydippinine Aa nd D, are presented for the first time.T he enantioenriched aza[3.3.1]bridged cycle,acommon core intermediate to the target molecules,w as constructed through an asymmetric phasetransfer-catalyzed Michael/aldol cascade reaction. The challenging azepane ring fused around the indole ring and the [3.3.1]-bridged cycle were installed through an intramolecular S N 2'-type reaction. These cyclization strategies enabled rapid construction of the [6.5.6.6.7]-pentacyclic core at an early stage.Highlights of the late-stage synthetic steps include aPd-catalyzedS tille coupling and ah ighly stereoselective catalystcontrolled hydrogenation to incorporate the side chain at C 20 with both Ra nd Sc onfigurations in the natural products. Figure 1. Structures of the dippinine/chippiine alkaloids.

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General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

Matheau‐Raven

Dixon

2021

Angewandte Chemie

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An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska's complex (IrCl(CO)(PPh 3) 2 ) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates. File list (2) download file view on ChemRxiv VaskaOxadiazoles -ChemRxiv.pdf (1.02 MiB) download file view on ChemRxiv VaskaOxadiazolesSI.pdf (4.98 MiB)

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Enantioselective Total Syntheses of Lyconadins A–E through a Palladium‐Catalyzed Heck‐Type Reaction

Cited by 9 publications

References 71 publications

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

Reaction-Based Multisignal Detection of Palladium with High Sensitivity, Selectivity, and Reliability

A Divergent Enantioselective Total Synthesis of Post‐Iboga Indole Alkaloids

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

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