ChemInform Abstract: A Synthetic Approach to Diverse 3‐Acyltetramic Acids via O‐ to C‐Acyl Rearrangement and Application to the Total Synthesis of Penicillenol Series.

Sengoku, Tetsuya; Nagae, Yuta; Ujihara, Yasuaki; Takahashi, Masaki; Yoda, Hidemi

doi:10.1002/chin.201235105

Cited by 4 publications

(4 citation statements)

References 1 publication

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“…The synthesis of a tetramic acid derivative (24 47 ) was accomplished according to known procedures in three steps, starting from N-Boc protected phenylalanine and Meldrum's acid, while structurally related cyclopentane-1,3-diones (25 and 26) were obtained via chemoselective benzylation of the appropriate isobutyl-protected cyclopentane-1,3-dione with benzyl bromide under conditions reported by Koreeda and co-workers, 48 followed by hydrolysis of the vinylogous ester (Scheme 8). The 1,3-dione derivative 27 was prepared in one step from cyclopentane-1,3-dione and benzaldehyde under reductive alkylation conditions.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Structure Property Relationships of Carboxylic Acid Isosteres

et al. 2016

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The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The dataset generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Structure Property Relationships of Carboxylic Acid Isosteres

et al. 2016

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“…5 Our retrosynthetic approach to macrocidin B isomer (5S,2′R,3′S,6′S,7′S)-2a is outlined in Scheme 1. It differs from our synthesis of macrocidin A, 3 where we 3-acylated a tyrosine-derived tetramic acid under Yoshii−Yoda conditions 6,7 (DMAP, NEt 3 , CaCl 2 ) with a carboxylic acid identical to 3 but lacking the β-OTBS group. This reaction proceeded via a 4-O-acyltetramate intermediate.…”

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confidence: 82%

Synthesis and Bioactivity of a Macrocidin B Stereoisomer

et al. 2021

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A stereoisomer of macrocidin B, a presumed metabolite of the fungus Phoma macrostoma, was synthesized in 18 steps and 2.7% yield from protected l-tyrosine that was N-β-ketoacylated with a fully functionalized octanoyl Meldrum’s acid. Dieckmann condensation gave a 3-acyltetramic acid, which was macrocyclized via Williamson etherification between the phenol and epi-bromohydrin termini. This macrocidin B stereoisomer showed a weaker herbicidal effect than macrocidin A and no similar inhibitory effect on biofilms of Staphylococcus aureus.

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“…(R)-4-Methylhexanoic Acid (14). According to a modified literature protocol, 11 a solution of alkene 13 (6.15 g, 43.65 mmol) in CH 2 Cl 2 p.a.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of the Entomopathogenic Fungus Metabolites Militarinone C and Fumosorinone A

2018

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Militarinone C and fumosorinone A, 3-oligoenoyltetramic acids produced by insect pathogenic fungi, were synthesized for the first time. The pyrrolidine-2,4-dione ring was closed through a late-stage Dieckmann condensation of N-(β-ketoacyl) derivatives of tyrosine, obtained by its acylation with either thioesters or Meldrum's acid derivatives bearing the all- trans-polyene side chain. The latter was built up from ( S)-citronellol via an Evans methylation and Wittig or HWE olefinations.

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ChemInform Abstract: A Synthetic Approach to Diverse 3‐Acyltetramic Acids via O‐ to C‐Acyl Rearrangement and Application to the Total Synthesis of Penicillenol Series.

Abstract: The efficient route to various biologically important 3‐acyltetramic acids can be applied to prepare penicillenol A2 (XIII).

Cited by 4 publications

References 1 publication

Structure Property Relationships of Carboxylic Acid Isosteres

Structure Property Relationships of Carboxylic Acid Isosteres

Synthesis and Bioactivity of a Macrocidin B Stereoisomer

Synthesis of the Entomopathogenic Fungus Metabolites Militarinone C and Fumosorinone A

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