Language：Japanese   Publisher：Scientific Reports  

Herein, we describe a highly potent gravitropic bending inhibitor with no concomitant growth inhibition. Previously, we reported that (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) selectively inhibits root gravitropic bending of lettuce radicles at 5 μM. Based on the structure–activity relationship study of ku-76 as a lead compound, we designed and synthesized various C4-substituted analogs of ku-76. Among the analogs, 4-phenylethynyl analog exhibited the highest potency for gravitropic bending inhibition, which was effective at only 0.01 μM. Remarkably, 4-phenylethynyl analog is much more potent than the known inhibitor, NPA. Substitution in the para position on the aromatic ring of 4-phenylethynyl group was tolerated without diminished activity. In addition, evaluation using Arabidopsis indicated that 4-phenylethynyl analog inhibits gravitropism by affecting auxin distribution in the root tips. Based on the effects on Arabidopsis phenotypes, 4-phenylethynyl analog may be a novel inhibitor that differs in action from the previously reported auxin transport inhibitors.

DOI： 10.1038/s41598-023-32063-z

Scopus

PubMed

Authorship：Lead author,　Corresponding author   Language：Japanese   Publisher：Advanced Synthesis and Catalysis  

With the aim of providing an efficient platform for the one-step construction of nitrogen-containing polycyclic frameworks, we report a heterogeneous platinum-catalyzed oxidative α,β-C(sp3)−H dual functionalization of saturated cyclic amines. This method involves a tandem oxidative dehydrogenation/hetero Diels-Alder reaction under aerobic mild conditions, providing tetracyclic octahydro-dipyrroloquinoline frameworks in good yields. The reaction was applied to the synthesis of natural products incargranine B aglycone and seneciobipyrrolidine in one step. This study provides efficient and rapid access to nitrogen-containing fused tetracyclic compounds in a highly atom-economical fashion. (Figure presented.).

DOI： 10.1002/adsc.202201332

Scopus

Language：Japanese   Publisher：The Society of Synthetic Organic Chemistry, Japan  

<p>Oxidation of aryl amines has been extensively utilized for the synthesis of nitrogen-containing functional materials. Among them, a number of methods for C-C bond forming reaction of aryl amines have been developed. Although oxidative biaryl coupling of aryl amines using stoichiometric metal or organic oxidants has been reported, the catalytic oxidation methods have been rarely studied to date. The aerobic oxidation is an attractive approach toward environmentally friendly synthesis of nitrogen-containing biaryl compounds. Recently, we developed a heterogeneous rhodium-catalyzed aerobic oxidative biaryl coupling reaction of aryl amines to provide various aminobiaryls such as BINAM derivatives, naphthidines, benzidines, and bicarbazoles. This heterogeneously catalyzed method can be adapted to highly selective cross-coupling reaction and the intramolecular biaryl coupling reaction of aryl amines. Additionally, we developed an aerobic direct C-H oxidation of polycyclic aromatics using a recyclable heterogeneous catalyst. In this account, our recent research activities regarding the heterogeneously catalyzed aerobic oxidative transformations of aromatic C-H bonds are described.</p>

DOI： 10.5059/yukigoseikyokaishi.79.755

Scopus

Authorship：Lead author,　Corresponding author   Language：Japanese   Publisher：Organic Letters  

DOI： 10.1021/acs.orglett.9b02527

Scopus

PubMed

Language：Japanese   Publisher：Journal of Organic Chemistry  

The reaction of 2-alkynylazetidines and alcohols with a gold catalyst is described. A variety of substituted δ-amino-α,β-unsaturated ketones were synthesized via gold-promoted nucleophilic attack of alcohols followed by ring-opening of azetidine ring.

DOI： 10.1021/acs.joc.2c01325

Scopus

PubMed

Authorship：Lead author,　Corresponding author  

J-GLOBAL

J-GLOBAL

J-GLOBAL

Language：Japanese   Publisher：(公財)薬学研究奨励財団  

Event date： 2023.8

Language：Japanese   Presentation type：Poster presentation  

Venue：東京、船堀  

Event date： 2023.3

Language：Japanese   Presentation type：Oral presentation (invited, special)  

Event date： 2023.3

Language：Japanese   Presentation type：Poster presentation  

Venue：札幌  

Event date： 2022.11

Language：Japanese   Presentation type：Poster presentation  

Venue：千葉  

Event date： 2022.11

Language：Japanese   Presentation type：Poster presentation  

Venue：千葉