Atsushi Nishida

Find an error

Name:

Organization: Chiba University

Department: Graduate School of Pharmaceutical Sciences

Title:

Chemicals
References

Abnormal Ito–Saegusa oxidation of TIPS enol ether assisted by a hydroxy group on a side chain

Co-reporter:Shiharu Hiraoka, Shinji Harada, Atsushi Nishida

Tetrahedron Letters 2011 Volume 52(Issue 24) pp:3079-3082

Publication Date(Web):15 June 2011

DOI:10.1016/j.tetlet.2011.03.119

Although Ito–Saegusa oxidation gives defined α,β-unsaturated ketones from silyl enol ether of ketones controlled by the position of the sp2 carbon of the silyl enol ether, the formation of a regioisomeric product that was oxidized abnormally was observed. The structural requirements for the substrates, the conditions, and a plausible mechanism are presented.

Reactivity and stereoselectivity of the Diels–Alder reaction using cyclic dienophiles and siloxyaminobutadienes

Co-reporter:Toshiyuki Ohfusa, Atsushi Nishida

Tetrahedron 2011 67(10) pp: 1893-1906

Publication Date(Web):

DOI:10.1016/j.tet.2011.01.019

Continuous-Flow CH Borylation of Arene Derivatives

Co-reporter:Tsuyoshi Tagata;Mayumi Nishida

Advanced Synthesis & Catalysis 2010 Volume 352( Issue 10) pp:1662-1666

Publication Date(Web):

DOI:10.1002/adsc.201000160

Abstract

A new continuous-flow system for CH borylation has been developed. An insoluble catalyst prepared from chloro(1,5-cyclooctadien)iridium(I) dimer and 2,2′-bipyridine-4,4′-dicarboxylic acid in the presence of bis(pinacolato)diboron exhibited high reactivity under continuous-flow processing without the loss of expensive iridium metal.

Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors

Co-reporter:Takayuki Watanabe, Mitsuhiro Arisawa, Kenji Narusuye, Mohommad Sayed Alam, Kazumi Yamamoto, Masaaki Mitomi, Yoshihisa Ozoe, Atsushi Nishida

Bioorganic & Medicinal Chemistry 2009 Volume 17(Issue 1) pp:94-110

Publication Date(Web):1 January 2009

DOI:10.1016/j.bmc.2008.11.017

The γ-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the development of a safer insecticide. In an attempt to obtain compounds with greater activity, a series of racemic alantrypinone derivatives were systematically synthesized using hetero Diels–Alder reactions, and a total of 34 compounds were examined for their ability to inhibit the specific binding of [3H]4′-ethynyl-4-n-propylbicycloorthobenzoate, a high-affinity non-competitive antagonist, to housefly-head membranes. The assay results showed that (1) there is no significant difference between the potencies of natural (+)-alantrypinone and its synthetic racemate; (2) the amide NHs at the 2- and 18-positions are important for high activity; (3) there is a considerable drop in potency for compounds without an aromatic ring at the 16-position; and (4) a large substituent at the 3-position is detrimental to high activity.

Development of recyclable iridium catalyst for C–H borylation

Co-reporter:Tsuyoshi Tagata, Mayumi Nishida, Atsushi Nishida

Tetrahedron Letters 2009 50(45) pp: 6176-6179

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.08.080

Highly enantioselective Diels–Alder reaction of Danishefsky-type diene and electron-deficient olefins catalyzed by an Yb(III)/chiral bis-urea complex

Co-reporter:Shinji Harada, Nozomi Toudou, Shiharu Hiraoka, Atsushi Nishida

Tetrahedron Letters 2009 50(40) pp: 5652-5655

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.07.110

Novel synthesis of fused indoles and 2-substituted indoles by the palladium-catalyzed cyclization of N-cycloalkenyl-o-haloanilines

Co-reporter:Jun Maruyama, Hiromichi Yamashita, Takeshi Watanabe, Shigeru Arai, Atsushi Nishida

Tetrahedron 2009 65(7) pp: 1327-1335

Publication Date(Web):

DOI:10.1016/j.tet.2008.12.028

Development of a Method for Preparing a Highly Reactive and Stable, Recyclable and Environmentally Benign Organopalladium Catalyst Supported on Sulfur-Terminated Gallium Arsenide(001): A Three-Component Catalyst, {Pd}-S-GaAs(001), and its Properties

Co-reporter:Mitsuhiro Arisawa;Masahiro Hamada;Ikuko Takamiya;Masahiko Shimoda;Shiro Tsukamoto;Yasuhiko Arakawa

Advanced Synthesis & Catalysis 2006 Volume 348(Issue 9) pp:

Publication Date(Web):28 JUN 2006

DOI:10.1002/adsc.200606025

We have developed a method for preparing a recyclable and environmentally benign organopalladium catalyst for the Heck reaction supported on sulfur-terminated gallium arsenide(001). This three-component catalyst, {Pd}-S-GaAs(001), exhibited high stability and activity, furthermore, it tolerated reuse in 10 runs of the Heck reaction (average yield, 97 %) under aerobic conditions. The sulfur layer was very important to stabilize this catalyst. Only trace amounts of Pd were leached from this catalyst to the reaction mixture, as measured by ICP-mass. The valence of immobilized Pd was zero by XPS spectrometry.

Total synthesis of (+)-(S)-angustureine and the determination of the absolute configuration of the natural product angustureine

Co-reporter:Chumpol Theeraladanon, Mitsuhiro Arisawa, Masako Nakagawa, Atsushi Nishida

Tetrahedron: Asymmetry 2005 Volume 16(Issue 4) pp:827-831

Publication Date(Web):21 February 2005

DOI:10.1016/j.tetasy.2004.12.022

Angustureine, isolated from the bark of Galipea officinalis Hancock, is a novel quinoline alkaloid with a n-pentyl side chain at the 2-position. The total synthesis of (+)-(S)-angustureine and a determination of the absolute configuration of the natural product angustureine were achieved using ring-closing metathesis (RCM) and the Mitsunobu reaction as key steps.The total synthesis of (+)-(S)-angustureine and a determination of the absolute configuration of the natural product angustureine were achieved using ring-closing metathesis (RCM) and the Mitsunobu reaction as key steps.N-Methyl-2-n-pentyl-1,2,3,4-tetrahydroquinolineC15H23NEe = 94%[α]D23=+7.9 (c 1.00, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)2-n-Pentyl-1,2,3,4-tetrahydroquinolineC14H21N[α]D23=-11.5 (c 1.00, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)N-p-Toluenesulfonyl-2-n-pentyl-1,2-dihydroquinolineC21H26NO2S[α]D23=-4.6 (c 1.00, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)N-(l-Pentyl-allyl)-N-p-toluenesulfonyl-2-ethynylanilineC23H30NO2S[α]D23=-36.6 (c 1.00, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)N-p-Toluenesulfonyl-2-n-pentyl-1,2,3,4-tetrahydroquinolineC21H28NO2SEe = 99%[α]D23=-121.4 (c 1.00, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

Cycloisomerization Promoted by the Combination of a Ruthenium–Carbene Catalyst and Trimethylsilyl Vinyl Ether, and its Application in The Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans

Co-reporter:Yukiyoshi Terada;Mitsuhiro Arisawa Dr. Dr.

Angewandte Chemie 2004 Volume 116(Issue 31) pp:

Publication Date(Web):2 AUG 2004

DOI:10.1002/ange.200454157

Substituierte N- und O-Heterocyclen wurden durch Cycloisomerisierung von Dienen mithilfe eines Rutheniumcarben-Katalysators hergestellt. Die mit und ohne Trimethylsilyl(vinyl)ether erhaltenen Produkte sind unterschiedlich (siehe Schema, Cy=Cyclohexyl, Mes=2,4,6-Trimethylphenyl, Ts=para-Toluolsulfonyl).

Asymmetric Total Synthesis of (−)-Nakadomarin A

Co-reporter:Koji Ono;Masako Nakagawa Dr. Dr.

Angewandte Chemie 2004 Volume 116(Issue 15) pp:

Publication Date(Web):30 MAR 2004

DOI:10.1002/ange.200453673

Schwammig: Ein wichtiges Zwischenprodukt in der asymmetrischen Synthese des marinen Alkaloids (−)-Nakadomarin A (1), isoliert aus dem Meeresschwamm Amphimedon sp., ist das optisch aktive Hydroisochinolin 2. Entscheidende Schritte beim Aufbau der 15- und 8-Ringe waren zwei Ringschlussmetathesen.

Asymmetric Total Synthesis of (−)-Nakadomarin A

Co-reporter:Koji Ono;Masako Nakagawa Dr. Dr.

Angewandte Chemie International Edition 2004 Volume 43(Issue 15) pp:

Publication Date(Web):30 MAR 2004

DOI:10.1002/anie.200453673

A key intermediate in the first asymmetric synthesis of the marine alkaloid (−)-nakadomarin A (1), isolated from the marine sponge Amphimedon sp., was the optically active hydroisoquinoline 2. Two separate ring-closing-metathesis reactions were crucial to the construction of the 15- and 8-membered rings.

Co-reporter:Yukiyoshi Terada;Mitsuhiro Arisawa Dr. Dr.

Angewandte Chemie International Edition 2004 Volume 43(Issue 31) pp:

Publication Date(Web):2 AUG 2004

DOI:10.1002/anie.200454157

Substituted N and O heterocycles have been synthesized by the cycloisomerization of dienes using a ruthenium-carbene catalyst. The products obtained with and without trimethylsilyl vinyl ether differ (see scheme, Cy=cyclohexyl, Mes=2,4,6-trimethylphenyl, Ts=p-toluenesulfonyl).

An efficient synthetic approach to optically active β-carboline derivatives via Pictet–Spengler reaction promoted by trimethylchlorosilane

Co-reporter:Riichiro Tsuji, Masako Nakagawa, Atsushi Nishida

Tetrahedron: Asymmetry 2003 Volume 14(Issue 2) pp:177-180

Publication Date(Web):17 January 2003

DOI:10.1016/S0957-4166(02)00793-0

A highly diastereoselective Pictet–Spengler reaction using chiral tryptamine carbamates has been developed. The reaction proceeds using aromatic and aliphatic aldehydes in the presence of trimethylchlorosilane.Graphic(1S)-1-Isopropyl-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl esterC31H40N2O2E.e.=100%[α]D26.5=−31.7 (c 1.85, CHCl3)Source of chirality: synthesis from l-tryptophan(1S)-1-Isopropyl-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid (1R,2S,5R)-5-methyl-2-[1-methyl-1-(4-phenoxyphenyl)-ethyl]cyclohexyl esterC37H44N2O3E.e.=100%[α]D26.5=+57.7 (c 1.01, CHCl3)Source of chirality: synthesis from l-tryptophan

Selective Isomerization of a Terminal Olefin Catalyzed by a Ruthenium Complex: The Synthesis of Indoles through Ring-Closing Metathesis

Co-reporter:Mitsuhiro Arisawa Dr.;Yukiyoshi Terada;Masako Nakagawa

Angewandte Chemie 2002 Volume 114(Issue 24) pp:

Publication Date(Web):12 DEC 2002

DOI:10.1002/ange.200290030

Ein Rutheniumkomplex, der aus dem Grubbs-Carbenkatalysator und Vinyloxytrimethylsilan hergestellt wurde, katalysiert die Isomerisierung von terminalen Alkenen RCH₂CHCH₂ zu internen Alkenen RCHCHCH₃. Die Anwendung dieser Olefinisomerisierung auf ein geschütztes 2-(N-Allylamino)styrol führte zu den entsprechenden Enaminen, die durch eine Standard-Ringschlussmetathese in Indole überführt wurden (siehe Schema, Ts=Tosyl).

Selective Isomerization of a Terminal Olefin Catalyzed by a Ruthenium Complex: The Synthesis of Indoles through Ring-Closing Metathesis

Co-reporter:Mitsuhiro Arisawa Dr.;Yukiyoshi Terada;Masako Nakagawa

Angewandte Chemie International Edition 2002 Volume 41(Issue 24) pp:

Publication Date(Web):12 DEC 2002

DOI:10.1002/anie.200290031

A ruthenium complex, generated from the Grubbs carbene catalyst with vinyloxytrimethylsilane, catalyzed the isomerization of terminal alkenes RCH₂CHCH₂ to internal alkenes RCHCHCH₃. Application of this olefin isomerization to 2-(N-allylamino)styrene gave the corresponding enamines, which were converted into indoles by a standard ring-closing metathesis, see scheme (Ts=tosyl).