Rapid mild macrocyclization of depsipeptides under continuous flow: total syntheses of five cyclodepsipeptides

Liao, Jingyuan; Jia, Xuelei; Wu, Fusong; Huang, Junrong; Shen, Guifu; You, Hengzhi; Chen, Fen‐Er

doi:10.1039/d2qo01577c

Cited by 3 publications

(3 citation statements)

References 47 publications

(56 reference statements)

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“…94 Utilizing CuBr$SMe 2 and phosphoramidite ligand L7 facilitated convenient access to optically pure cycloalkene derivatives. Furthermore, the catalytic enantioselective allylic alkylation processes have been successfully adapted to continuous ow techniques, [95][96][97][98][99][100] but only with 33% e.e. The difference in the contact mode between batch and ow reactions primarily led to a decrease in enantioselectivities.…”

Section: Direct Enantioconvergent Transformationmentioning

confidence: 99%

Copper-catalyzed asymmetric allylic substitution of racemic/meso substrates

Li,

Huang,

Wang

et al. 2024

Chem. Sci.

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Section: Direct Enantioconvergent Transformationmentioning

confidence: 99%

Copper-catalyzed asymmetric allylic substitution of racemic/meso substrates

Li,

Huang,

Wang

et al. 2024

Chem. Sci.

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“…Thus, developing continuous flow chemistry for the macrolactonization could control the various limitations that arise from the batch reactions. However, to the best of our knowledge, there is only one recent report available in the literature for continuous flow macrolactonization using a coupling reagent …”

Section: Introductionmentioning

confidence: 99%

“…However, to the best of our knowledge, there is only one recent report available in the literature for continuous flow macrolactonization using a coupling reagent. 27 Continuous flow chemistry is a well-established technique used for the large-scale production of intermediates and pharmaceutical drugs. 28 On the other hand, the traditional batch method required very harsh reaction conditions as the reflux setups with round-bottom flasks (RBFs) where the scaleup of the optimized process is very challenging due to the need for many other additional adjustments.…”

Section: ■ Introductionmentioning

confidence: 99%

Continuous Flow Inter- and Intramolecular Macrolactonization under High Dilution Conditions

et al. 2023

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An efficient continuous flow process for the macrolactonization of seco acids and diacids using diols in the presence of Mukaiyama reagent (N-methyl-2-chloropyridinium iodide) has been developed for medium to large sized macrocyclic lactones. In comparison with other methods, the continuous flow process provided good to high yield in a short reaction time. By using this methodology, a wide range of macrocyclic lactones (11 compounds), dilactones (15 compounds), and tetralactone derivatives (2 compounds) with various ring sizes (12–26 atoms in the core) were synthesized in just 35 min of residence time. Advantageously, macrolactonization under the flow process is very elegant to handle the high dilution of reactants with a defined perfluoroalkoxy alkanes (PFA) tube reactor volume (7 mL).

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Origin and characterization of cyclodepsipeptides: Comprehensive structural approaches with focus on mass spectrometry analysis of alkali‐cationized molecular species

Liuu,

Damont,

Perret

et al. 2024

Mass Spectrometry Reviews

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Cyclodepsipeptides (CDPs) represent a huge family of chemically and structurally diverse molecules with a wide ability for molecular interactions. CDPs are cyclic peptide‐related natural products made up of both proteinogenic and nonproteinogenic amino acids linked by amide and ester bonds. The combined use of different analytical methods is required to accurately determine their integral structures including stereochemistry, thus allowing deeper insights into their often‐intriguing bioactivities and their possible usefulness. Our goal is to present the various methods developed to accurately characterize CDPs. Presently, Marfey's method and NMR (nuclear magnetic resonance) are still considered the best for characterizing CDP configuration. Nevertheless, electrospray‐high resolution tandem mass spectrometry (ESI‐HRMS/MS) is of great value for efficiently resolving CDP's composition and sequences. For instance, recent data shows that the fragmentation of cationized CDPs (e.g., [M + Li]+ and [M + Na]+) leads to selective cleavage of ester bonds and specific cationized product ions (b series) useful to get unprecedented sequence information. Thus, after a brief presentation of their structure, biological functions, and biosynthesis, we also provide a historic overview of these various analytical approaches as well as their advantages and limitations with a special emphasis on the emergence of methods based on HRMS/MS through recent fundamental works and applications.

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Rapid mild macrocyclization of depsipeptides under continuous flow: total syntheses of five cyclodepsipeptides

Abstract: The total synthesis of five natural products Destruxin B, Pseudodestruxin B, Isaridin A, Cladoamide A, and Cladoamide B was accomplished. These depsipeptides were synthesized though a flow macrocyclization method from...

Cited by 3 publications

References 47 publications

Copper-catalyzed asymmetric allylic substitution of racemic/meso substrates

Copper-catalyzed asymmetric allylic substitution of racemic/meso substrates

Continuous Flow Inter- and Intramolecular Macrolactonization under High Dilution Conditions

Origin and characterization of cyclodepsipeptides: Comprehensive structural approaches with focus on mass spectrometry analysis of alkali‐cationized molecular species

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