Yoo Tanabe

Kwansei Gakuin University

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Tomonori Misaki

Fukui Prefectural Hospital

Yoshinori Nishii

Shinshu University

Hidefumi Nakatsuji

Kwansei Gakuin University

Ryohei Nagase

Kwansei Gakuin University

Akira Iida

Kindai University

Kazunori Wakasugi

Eisai (Japan)

Yuichiro Ashida

Kwansei Gakuin University

Yuzuru Sanemitsu

Tokyo University of Agriculture

Jun‐ichi Morita

Kwansei Gakuin University

Yoshihiro Yoshida

Tokyo Metropolitan University

Cooperative Institutions

Kwansei Gakuin University

146

Kyoto University

The University of Tokyo

Osaka University

Tokyo University of Pharmacy and Life Sciences

Wuhan Institute of Technology

Hubei University

University of Auckland

Banaras Hindu University

Lishui University

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Total synthesis of (−)-periplanones C and D. Their pheromonal activities against three Periplaneta species

Tetrahedron (1997)

Yoshinori Nishii Keisuke Watanabe Taichi Yoshida Tatsutoshi Okayama Shozo Takahashi

10.1016/s0040-4020(97)00424-9

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Citations (8)

(E)- and (Z)-stereodefined enol phosphonates derived from β-ketoesters: stereocomplementary synthesis of fully-substituted α,β-unsaturated esters

Organic & Biomolecular Chemistry (2015)

Hidefumi Nakatsuji Yuichiro Ashida Hiroshi Hori Yuka Sato Atsushi Honda

A versatile, robust, and stereocomplementary synthesis of fully-substituted (E)- and (Z)-stereodefined α,β-unsaturated esters 3 from accessible α-substituted β-ketoesters 1via (E)- and (Z)-enol phosphonates was achieved.

Negishi coupling

Coupling reaction

Proton NMR

10.1039/c5ob01097g

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Citations (25)

A Highly Efficient Synthesis of Civetone

Tetrahedron (2000)

Ryota Hamasaki Syunsuke Funakoshi Tomonori Misaki Yoo Tanabe

Olefin Metathesis

Claisen condensation

Salt metathesis reaction

Acyclic diene metathesis

Condensation reaction

10.1016/s0040-4020(00)00654-2

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Citations (33)

Benzyl (R)-2-(Acetylthio)Propanoate: A Promising Sulfur Isoster of (R)-Lactic Acid and Ester Precursors

Molbank (2018)

Ryosuke Sasaki Momoyo Kawamoto Yoo Tanabe

In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean SN2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially available benzyl (S)-lactate in 76%, 94% ee (2 steps). Deprotection of the acetyl group using N,N-dimethylethylenediamine afforded benzyl (R)-2-sulfanylpropanoate in 93% yield with 90% ee. These two sulfur-containing benzyl esters were sufficiently odorless to be purified by column chromatography. Direct HPLC analysis was applied to determine the enantiomeric excess without thiazolidin-4-one derivatizations. A complementary debenzylation of benzyl (R)-2-(acetylthio)propanoate was also performed using HBr/AcOH to afford (R)-2-(acetylthio)propanoic acid without critical racemization in 92% yield with 92% ee.

Propanoic acid

Racemization

Diastereomer

Benzyl alcohol

SN2 reaction

10.3390/m1010

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Novel method for the synthesis of α- and β-halogenonaphthalenes by regioselective benzannulation of aryl(gem-dihalogenocyclopropyl)methanols: application to the total synthesis of the lignan lactones, justicidin E and taiwanin C¹

Journal of the Chemical Society. Perkin transactions I/Journal of the Chemical Society. Perkin transactions. I (1996)

Yoo Tanabe Shinzo Seko Yoshinori Nishii Taichi Yoshida Naoka Utsumi

Acid treatment of two types of aryl(gem-dihalogenocyclopropyl)methanols (ADCMs) 1 and 3 gives α- and β-halogenonaphthalenes in good yields with excellent selectivity. These alternative annulations involve two distinctive types of highly regioselective acid-induced cyclopropane ring cleavage, wherein the preferential formation of more stable cationic intermediates determines the selectivity. The stereochemical mode of both the preparation and the annulation between diastereoisomers of an ADCM has been checked. As a demonstration of this annulation, a total synthesis of each of the natural lignan lactones, justicidin E 19 and taiwanin C 20, has also been performed. Since these 4-arylnaphthalenes are expected to exhibit biological activity, the anti-platelet activating factor (anti-PAF) activity of justicidin E has been assayed.

Annulation

Diastereomer

Cyclopropane

Cationic polymerization

10.1039/p19960002157

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Citations (39)

A Convenient Synthesis of 3-Chloromethyl-2(3H)-benzothiazolones

Synthesis (1988)

Yoo Tanabe Yuzuru Sanemitsu

3-Chloromethyl-2(3H)-benzothiazolones 4 were synthesized from 1,3, 5-triphenyl-1,3,5-triazines 2 and chlorocarbonylsulfenyl chloride in a one-pot procedure. The chlorine atom in 4 was subtituted by three types of nucleophiles, namely, potassium acetate, p-toluenethiolate ion and sodium azide, in good yield.

Sodium azide

Chlorine atom

Sodium acetate

10.1055/s-1988-27616

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Citations (9)

Aza-Diels−Alder Reaction of Methyl 2-[(R)-1-Phenylethyl]iminoethanoate with Cyclopentadiene Using Practical and Environmentally Friendly Biphasic Solvent System

Organic Process Research & Development (2004)

Norio Hashimoto Hironobu Yasuda Masaru Hayashi Yoo Tanabe

Aza-Diels−Alder reaction between 2-[(R)-1-phenylethyl]iminoethanoate (1) and cyclopentadiene using the biphasic solvent system (TMSCl−CH3OH/toluene) gave (1S,3S,4R)-2-[(R)-1-phenylethyl]-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylates (3a) in 32% isolated yield. The present method is advantageous for the large-scale synthesis, because (i) the reported methods required harmful and expensive fluorinated chemicals, (ii) methyl analogue 3a was practically isolated as a crystalline solid, and (iii) the reaction was conducted with very little observable exotherm. In addition, the absolute configurations of the other three diastereomers 2, 4, and 5 were unambiguously determined.

Cyclopentadiene

Diastereomer

Diels–Alder reaction

Environmentally Friendly

10.1021/op049828m

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Citations (21)

Sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-l-naphthol derivatives

Tetrahedron Letters (1995)

Yoshinori Nishii Yoo Tanabe

Friedel–Crafts reaction

Cyclopropane

10.1016/0040-4039(95)01866-g

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Citations (20)

Cyclopropane-shift type reaction of diaryl(2-halogenocyclopropyl)methanols promoted by Lewis acids

Tetrahedron Letters (2000)

Kazunori Wakasugi Yoshinori Nishii Yoo Tanabe

Cyclopropane

10.1016/s0040-4039(00)00979-5

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Citations (12)

ChemInform Abstract: Powerful Stereoselective Aldol‐Type Additions of Phenyl and Phenylthio Esters with Aldehydes or Ketones Mediated by TiCl₄/Amine Reagent.

ChemInform (2002)

Yoo Tanabe Noriaki Matsumoto Syunsuke Funakoshi Naoki Manta

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Aldol reaction

Addition reaction

10.1002/chin.200214095

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Citations (0)