Total synthesis of lycoperdic acid and its C4-epimer

Morokuma, Kenji; Irie, Raku; Oikawa, Masato

doi:10.1016/j.tetlet.2019.06.067

Cited by 11 publications

(4 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction afforded an inseparable 1.13:1 mixture of the (2S,4S)-isomer with the natural configuration (93.5% ee) and the unnatural (2S,4R)isomer (>99.8% ee) (Scheme 9). 14…”

Section: Methodsmentioning

confidence: 99%

Recent Developments in Transition-Metal-Catalyzed Asymmetric Hydrogenation of Enamides

et al. 2020

View full text Add to dashboard Cite

The catalytic asymmetric hydrogenation of prochiral olefins is one of the most widely studied and utilized transformations in asymmetric synthesis. This straightforward, atom economical, inherently direct and sustainable strategy induces chirality in a broad range of substrates and is widely relevant for both industrial applications and academic research. In addition, the asymmetric hydrogenation of enamides has been widely used for the synthesis of chiral amines and their derivatives. In this review, we summarize the recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of enamides.1 Introduction2 Asymmetric Hydrogenation of Trisubstituted Enamides2.1 Ruthenium Catalysts2.2 Rhodium Catalysts2.3 Iridium Catalysts2.4 Nickel Catalysts2.5 Cobalt Catalysts3 Asymmetric Hydrogenation of Tetrasubstituted Enamides3.1 Ruthenium Catalysts3.2 Rhodium Catalysts3.3 Nickel Catalysts4 Asymmetric Hydrogenation of Terminal Enamides4.1 Rhodium Catalysts4.2 Cobalt Catalysts5 Rhodium-Catalyzed Asymmetric Hydrogenation of Miscellaneous Enamides6 Conclusions

show abstract

“…The reaction afforded an inseparable 1.13:1 mixture of the (2S,4S)-isomer with the natural configuration (93.5% ee) and the unnatural (2S,4R)isomer (>99.8% ee) (Scheme 9). 14…”

Section: Methodsmentioning

confidence: 99%

Recent Developments in Transition-Metal-Catalyzed Asymmetric Hydrogenation of Enamides

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Additional analysis of the DEMs of gylc and qmlc (Supplementary Table 1) revealed that lycoperdic acid and citrinin were up-regulated, while nivalenol and validamycin B were down-regulated in gylc. The synthesis of lycoperdic acid imparts a pungent odor and antibacterial properties to the sporophore of Lycoperdon perlatum (33). The study performed by Bryla et al found that Nivalenol produced by Fusarium graminearum (34) was downregulated greatly.…”

Section: Metabolic Differences Between Gylc and Qmlcmentioning

confidence: 99%

The molecular mechanisms of quality difference for Alpine Qingming green tea and Guyu green tea by integrating multi-omics

et al. 2023

View full text Add to dashboard Cite

IntroductionHarvest time represents one of the crucial factors concerning the quality of alpine green tea. At present, the mechanisms of the tea quality changing with harvest time have been unrevealed.MethodsIn the current study, fresh tea leaves (qmlc and gylc) and processed leaves (qmgc and gygc) picked during Qingming Festival and Guyu Festival were analyzed by means of sensory evaluation, metabolomics, transcriptomic analysis, and high-throughput sequencing, as well as their endophytic bacteria (qm16s and gy16s).ResultsThe results indicated qmgc possessed higher sensory quality than gygc which reflected from higher relative contents of amino acids, and soluble sugars but lower relative contents of catechins, theaflavins, and flavonols. These differential metabolites created features of light green color, prominent freshness, sweet aftertaste, and mild bitterness for qmgc.DiscussionFlavone and flavonol biosynthesis and phenylalanine metabolism were uncovered as the key pathways to differentiate the quality of qmgc and gygc. Endophytic bacteria in leaves further influence the quality by regulating the growth of tea trees and enhancing their disease resistance. Our findings threw some new clues on the tea leaves picking to pursue the balance when facing the conflicts of product quality and economic benefits.

show abstract

“…(+)-Lycoperdic acid ( 1 ) was isolated from a mushroom Lycoperdon perlatum by Rhugenda-Banga et al It is an amino acid that shares structural similarities with both l -glutamic acid ( 2 ) and dysiherbaines ( 3a , 3b , Figure ). , The dysiherbaines are well-known ionotropic glutamate receptor binders, , a fact which has raised questions about the biological activity of (+)- 1 over the years. − …”

mentioning

confidence: 99%

“…To date, there are seven total syntheses and one formal synthesis for (+)- 1 . − Most of them rely on either chiral pool or chiral auxiliaries to set the stereochemistry at C2 and C4 (Figure ). Very recently, the Oikawa group disclosed an approach where catalytic enantioselective hydrogenation was used to control the stereochemistry at C2 of (+)- 1 , but the construction of C4 was not stereoselective …”

mentioning

confidence: 99%