Syntheses of natural 1,3-polyol/α-pyrone and its all stereoisomers to estimate antifungal activities against plant pathogenic fungi

Yamauchi, Satoshi; Isozaki, Yasuyoshi; Nishiwaki, Hisashi; Akiyama, Koichi

doi:10.1016/j.bmcl.2015.03.055

Cited by 4 publications

(2 citation statements)

References 28 publications

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“…It is known that organic compounds having biological activities differ in these activities between stereoisomers [21][22][23][24][25]. As thioamides showing antibacterial activities have an asymmetric center at the C-5 position, it is considered that there is a difference in antibacterial properties between the stereoisomers.…”

Section: Diastereomeric Resolution Of Racemic 5-hydroxyalkanethioamidmentioning

confidence: 99%

“…Based on these facts, we synthesized various N-methyl-5-acetoxyalkanethioamides and attempted to improve their antibacterial activities and establish the structure-activity relationship. In many cases, there is a difference in biological activity between stereoisomers [21][22][23][24][25]. Therefore, optically active N-methyl-5-acetoxyalkanethioamides were synthesized, and their antibacterial activities were evaluated.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- and 5-acetoxyalkanethioamide analogues

Shimotori

Hoshi

Ogawa

et al. 2020

Heterocyclic Communications

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Abstract5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. Therefore, these thioamides are potential sustained-release perfume compounds having antibacterial properties.

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Section: Diastereomeric Resolution Of Racemic 5-hydroxyalkanethioamidmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- and 5-acetoxyalkanethioamide analogues

Shimotori

Hoshi

Ogawa

et al. 2020

Heterocyclic Communications

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Discussion Addendum For: Protection of Alcohols Using 2‐Benzyloxy‐1‐Methylpyridinium Trifluoromethanesulfonate: Methyl ( R )‐(‐)‐3‐Benzyloxy‐2‐methyl Propanoate

2020

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Benzyl ethers are important protecting groups in organic synthesis, but traditional installation methods, such as the Williamson ether synthesis or reaction of an alcohol with benzyl trichloroacetimidate, often limit their formation with substrates containing functional groups unable to tolerate strongly basic or acidic conditions, respectively. The reaction of N,N‐dimethylaniline occurred via an N‐methyl to benzyl exchange instead of the expected electrophilic aromatic substitution. This illustrates that amines can also trap the putative phenylcarbenium species released during the thermal activation of 2‐benzyloxy‐1‐methylpyridinium triflate (BnOPT). Benzylation can generally be achieved chemoselectively using BnOPT with triethylamine in the presence of alcohols, amides, and other functional groups. The mild and nearly neutral conditions associated with the use of BnOPT is the main advantage of the benzylation protocol.

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Syntheses and Phytotoxicity of All Stereoisomers of 6-(2-Hydroxy-6-phenylhex-1-yl)-5,6-dihydro-2H-pyran-2-one and Determination of the Effect of the α,β-Unsaturated Carbonyl Structure and Hydroxy Group Bonding to Chiral Carbon

Ochi

Nishiwaki

Yamauchi

2019

J. Agric. Food Chem.

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Syntheses of natural 1,3-polyol/α-pyrone and its all stereoisomers to estimate antifungal activities against plant pathogenic fungi

Cited by 4 publications

References 28 publications

Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- and 5-acetoxyalkanethioamide analogues

Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- and 5-acetoxyalkanethioamide analogues

Discussion Addendum For: Protection of Alcohols Using 2‐Benzyloxy‐1‐Methylpyridinium Trifluoromethanesulfonate: Methyl ( R )‐(‐)‐3‐Benzyloxy‐2‐methyl Propanoate

Syntheses and Phytotoxicity of All Stereoisomers of 6-(2-Hydroxy-6-phenylhex-1-yl)-5,6-dihydro-2H-pyran-2-one and Determination of the Effect of the α,β-Unsaturated Carbonyl Structure and Hydroxy Group Bonding to Chiral Carbon

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