start-ver=1.4
cd-journal=joma
no-vol=
cd-vols=
no-issue=
article-no=
start-page=e202301130
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2023
dt-pub=20231219
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Concise Synthesis of Thiazolo[4,5-b]indoles via Ring Switch/Cyclization Sequences
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=The unexpected reactions of indoline hemiaminals affords 2,5-diaryl-4-hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance (17 examples, up to 99?% yield). Further transformations of the thiazolines provide a direct entry to dihydrothiazolo[4,5-b]indoles and thiazolo[4,5-b]indoles.
en-copyright=
kn-copyright=

en-aut-name=YamadaKoji
en-aut-sei=Yamada
en-aut-mei=Koji
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=TsubogoTetsu
en-aut-sei=Tsubogo
en-aut-mei=Tetsu
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

en-aut-name=KanazawaHikaru
en-aut-sei=Kanazawa
en-aut-mei=Hikaru
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=

en-aut-name=IshizukaSayaka
en-aut-sei=Ishizuka
en-aut-mei=Sayaka
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=

en-aut-name=OhyamaKoutaro
en-aut-sei=Ohyama
en-aut-mei=Koutaro
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=

en-aut-name=KaidaMasaki
en-aut-sei=Kaida
en-aut-mei=Masaki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=6
ORCID=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=7
ORCID=

affil-num=1
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido
kn-affil=

affil-num=2
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido
kn-affil=

affil-num=3
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido
kn-affil=

affil-num=4
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido
kn-affil=

affil-num=5
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido
kn-affil=

affil-num=6
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido
kn-affil=

affil-num=7
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
en-keyword=hemiaminals
kn-keyword=hemiaminals
en-keyword=indoles
kn-keyword=indoles
en-keyword=ring-switch
kn-keyword=ring-switch
en-keyword=thiazolo[4.5-b]indoles
kn-keyword=thiazolo[4.5-b]indoles
en-keyword=thioamides
kn-keyword=thioamides
END

start-ver=1.4
cd-journal=joma
no-vol=85
cd-vols=
no-issue=8
article-no=
start-page=2122
end-page=2125
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2022
dt-pub=20220817
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=First Total Synthesis of Reassigned Echinosulfonic Acid D
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=Echinosulfonic acid D, a sponge metabolite whose structure was recently reassigned, was synthesized for the first time. The key step is the double indolization of dimethylbarbituric acid using the umpolung indole reagent, followed by a hydrolysis/decarboxylation/esterification sequence.
en-copyright=
kn-copyright=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=NakajimaRen
en-aut-sei=Nakajima
en-aut-mei=Ren
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

en-aut-name=YamashiroToshiki
en-aut-sei=Yamashiro
en-aut-mei=Toshiki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=

en-aut-name=SawadaDaisuke
en-aut-sei=Sawada
en-aut-mei=Daisuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=3
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=4
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
END

start-ver=1.4
cd-journal=joma
no-vol=28
cd-vols=
no-issue=37
article-no=
start-page=e202201113
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2022
dt-pub=20220519
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Indole Editing Enabled by HFIP]Mediated Ring]Switch Reactions of 3]Amino]2]Hydroxyindolines
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=We found the novel reactivity of hemiaminal as a precursor for indole editing at the multi-site. The HFIP-promoted indole editing of indoline hemiaminals affords 2-arylindoles through a ring-switch sequence. The key to success of this transformation is to use a cyclic hemiaminal as an a-amino aldehyde surrogate under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance. The utility of this transformation is presented through the one-pot protocol and the synthesis of isocryptolepine.
en-copyright=
kn-copyright=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=YamashiroToshiki
en-aut-sei=Yamashiro
en-aut-mei=Toshiki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

en-aut-name=ShimizuKaho
en-aut-sei=Shimizu
en-aut-mei=Kaho
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=

en-aut-name=SawadaDaisuke
en-aut-sei=Sawada
en-aut-mei=Daisuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=3
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=4
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
en-keyword=hemiaminals
kn-keyword=hemiaminals
en-keyword=HFIP
kn-keyword=HFIP
en-keyword=indoles
kn-keyword=indoles
en-keyword=molecule editing
kn-keyword=molecule editing
en-keyword=ring-switch
kn-keyword=ring-switch
END

start-ver=1.4
cd-journal=joma
no-vol=
cd-vols=
no-issue=
article-no=
start-page=e202302963
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2024
dt-pub=20240108
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=On Demand Synthesis of C3?N1f Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (})]Rivularin A
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=In this work, a straightforward synthesis of C3?N1f bisindolines is achieved by a formal umpolung strategy. The protocols were tolerant of a wide variety of substituents on the indole and indoline ring. In addition, the C3?N1f bisindolines could be converted to C3?N1f indole-indolines and C3?N1f-bisindoles. Also, we have successfully synthesized (})-rivularin A through a biomimetic late-stage tribromination as a key step.
en-copyright=
kn-copyright=

en-aut-name=TokushigeKeisuke
en-aut-sei=Tokushige
en-aut-mei=Keisuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
en-keyword=C3-N1' bisindoles
kn-keyword=C3-N1' bisindoles
en-keyword=bromination
kn-keyword=bromination
en-keyword=umpolung
kn-keyword=umpolung
en-keyword=rivularin A
kn-keyword=rivularin A
en-keyword=alkaloid
kn-keyword=alkaloid
END

start-ver=1.4
cd-journal=joma
no-vol=88
cd-vols=
no-issue=14
article-no=
start-page=9920
end-page=9926
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2023
dt-pub=20230711
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Oxytrofalcatin Puzzle: Total Synthesis and Structural Revision of Oxytrofalcatins B and C
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=The previously reported structures of oxytrofalcatins B and C possess a benzoyl indole core. However, following synthesis and NMR comparison of both the proposed structure and the synthesized oxazole, we have revised the structure of oxytrofalcatins B and C as oxazoles. The synthetic route developed herein can further our understanding of the biosynthetic pathways that govern the production of natural 2,5-diaryloxazoles.
en-copyright=
kn-copyright=

en-aut-name=SugitateKazuma
en-aut-sei=Sugitate
en-aut-mei=Kazuma
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=YamashiroToshiki
en-aut-sei=Yamashiro
en-aut-mei=Toshiki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

en-aut-name=TakahashiIbuki
en-aut-sei=Takahashi
en-aut-mei=Ibuki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=

en-aut-name=YamadaKoji
en-aut-sei=Yamada
en-aut-mei=Koji
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=3
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-tobetsu, Hokkaido 0610293, Japan
kn-affil=

affil-num=4
en-affil=Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido
kn-affil=

affil-num=5
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
END

start-ver=1.4
cd-journal=joma
no-vol=24
cd-vols=
no-issue=5
article-no=
start-page=4411
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2023
dt-pub=20230223
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Revisiting Cryptocyanine Dye, NK-4, as an Old and New Drug: Review and Future Perspectives
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=NK-4 plays a key role in the treatment of various diseases, such as in hay fever to expect anti-allergic effects, in bacterial infections and gum abscesses to expect anti-inflammatory effects, in scratches, cuts, and mouth sores from bites inside the mouth for enhanced wound healing, in herpes simplex virus (HSV)-1 infections for antiviral effects, and in peripheral nerve disease that causes tingling pain and numbness in hands and feet, while NK-4 is used also to expect antioxidative and neuroprotective effects. We review all therapeutic directions for the cyanine dye NK-4, as well as the pharmacological mechanism of NK-4 in animal models of related diseases. Currently, NK-4, which is sold as an over-the-counter drug in drugstores, is approved for treating allergic diseases, loss of appetite, sleepiness, anemia, peripheral neuropathy, acute suppurative diseases, wounds, heat injuries, frostbite, and tinea pedis in Japan. The therapeutic effects of NK-4fs antioxidant and neuroprotective properties in animal models are now under development, and we hope to apply these pharmacological effects of NK-4 to the treatment of more diseases. All experimental data suggest that different kinds of utility of NK-4 in the treatment of diseases can be developed based on the various pharmacological properties of NK-4. It is expected that NK-4 could be developed in more therapeutic strategies to treat many types of diseases, such as neurodegenerative and retinal degenerative diseases.
en-copyright=
kn-copyright=

en-aut-name=LiuShihui
en-aut-sei=Liu
en-aut-mei=Shihui
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=MatsuoToshihiko
en-aut-sei=Matsuo
en-aut-mei=Toshihiko
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=

affil-num=1
en-affil=Graduate School of Interdisciplinary Science and Engineering in Health Systems, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Interdisciplinary Science and Engineering in Health Systems, Okayama University
kn-affil=

affil-num=3
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
END

start-ver=1.4
cd-journal=joma
no-vol=9
cd-vols=
no-issue=7
article-no=
start-page=1897
end-page=1903
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2022
dt-pub=2022
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Synthesis of 2-monosubstituted indolin-3-ones by cine-substitution of 3-azido-2-methoxyindolines
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=We report herein a formal cine-substitution/hydrolysis of 3-azidoindoles generated from 3-azido-2-methoxyindolines (AZINs). This protocol enables the introduction of various carboxylic acids and alcohols into indolin-3-ones at the C2-position, affording 2-monoacyloxy or alkoxy indolin-3-ones.
en-copyright=
kn-copyright=

en-aut-name=YamashiroToshiki
en-aut-sei=Yamashiro
en-aut-mei=Toshiki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

en-aut-name=SawadaDaisuke
en-aut-sei=Sawada
en-aut-mei=Daisuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=3
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
END

start-ver=1.4
cd-journal=joma
no-vol=
cd-vols=
no-issue=
article-no=
start-page=
end-page=
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2024
dt-pub=2024
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Synthetic strategies for the construction of C3?N1Œ bisindoles
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=C3?N1Œ bisindoles are unique structures, and the construction of these structures has drawn much attention. However, their synthesis still presents significant challenges that limit the functional group compatibility. This minireview summarizes the recent progress in the methodology for constructing C3?N1Œ bisindoles. There are two approaches for access to C3?N1Œ bisindoles: (1) direct approaches including reverse polarity techniques. (2) Stepwise approaches using designed and prefunctionalized substrates enable further functionalization by additional reactions to facilitate access to the target products. I believe that this review will allow its readers to develop novel approaches for the synthesis of C3?N1Œ bisindoles.
en-copyright=
kn-copyright=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
END

start-ver=1.4
cd-journal=joma
no-vol=5
cd-vols=
no-issue=4
article-no=
start-page=2772
end-page=2784
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2023
dt-pub=20231212
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=Total Synthesis of the Proposed Structure of Indolyl 1,2-Propanediol Alkaloid, 1-(1H-Indol-3-yloxy)propan-2-ol
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=The first total synthesis of the proposed structure of unprecedented indolyl derivative bearing 1,2-propanediol moiety is described. Isomerization of 3-alkoxyindolines through indolenium intermediates was the key step in the total synthesis. H-1, C-13-NMR, IR, and HRMS spectra of the synthetic compound drastically differed to those of the originally reported structure, which suggests the natural product requires revision.
en-copyright=
kn-copyright=

en-aut-name=KimataMomoko
en-aut-sei=Kimata
en-aut-mei=Momoko
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
en-keyword=1-(1H-indol-3-yloxy)propan-2-ol
kn-keyword=1-(1H-indol-3-yloxy)propan-2-ol
en-keyword=indole alkaloid
kn-keyword=indole alkaloid
en-keyword=isomerization
kn-keyword=isomerization
en-keyword=silver
kn-keyword=silver
en-keyword=umpolung
kn-keyword=umpolung
END

start-ver=1.4
cd-journal=joma
no-vol=57
cd-vols=
no-issue=
article-no=
start-page=13381
end-page=13384
dt-received=
dt-revised=
dt-accepted=
dt-pub-year=2021
dt-pub=20211116
dt-online=
en-article=
kn-article=
en-subject=
kn-subject=
en-title=
kn-title=cis-3-Azido-2-methoxyindolines as safe and stable precursors to overcome the instability of fleeting 3-azidoindoles
en-subtitle=
kn-subtitle=
en-abstract=
kn-abstract=Use of 3-azidoindoles in organic synthesis remains a difficult task owing to their instabilities. Herein, we report a general and concise approach for tackling this problem by using 3-azidoindole surrogates. The surrogates are bench-stable, presumably due to the observed intramolecular O-N-beta bonding. The resultant fleeting intermediates undergo capturing in situ to afford 3-substitued indoles through formal ipso-substitution of the azide group by nucleophiles. In these investigations, we found that the fleeting 3-azidoindoles show a C3-electrophilic character for the first time.
en-copyright=
kn-copyright=

en-aut-name=YamashiroToshiki
en-aut-sei=Yamashiro
en-aut-mei=Toshiki
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=1
ORCID=

en-aut-name=AbeTakumi
en-aut-sei=Abe
en-aut-mei=Takumi
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=2
ORCID=

en-aut-name=TaniokaMasaru
en-aut-sei=Tanioka
en-aut-mei=Masaru
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=3
ORCID=

en-aut-name=KaminoShinichiro
en-aut-sei=Kamino
en-aut-mei=Shinichiro
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=4
ORCID=

en-aut-name=SawadaDaisuke
en-aut-sei=Sawada
en-aut-mei=Daisuke
kn-aut-name=
kn-aut-sei=
kn-aut-mei=
aut-affil-num=5
ORCID=

affil-num=1
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=2
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=

affil-num=3
en-affil=School of Pharmaceutical Sciences, Aichi Gakuin University
kn-affil=

affil-num=4
en-affil=School of Pharmaceutical Sciences, Aichi Gakuin University
kn-affil=

affil-num=5
en-affil=Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
kn-affil=
END