1,6-Asymmetric Induction by Reductive Acetal Cleavage of a Bicyclic Acetal Using a Sulfinyl Chiral Auxiliary

スポンサーリンク

概要

• 論文の詳細を見る

• A new synthetic route to a chiral 2,5-disubstituted tetrahydropyran has been achieved by asymmetric reductive acetal cleavage of a bicyclic acetal having a chiral sulfinyl group as a chiral auxiliary. It was found that the (5S)-tetrahydropyran was obtained preferentially (up to 96 : 4) with an R-sulfinyl chiral auxiliary by an efficient 1,6-asymmetric induction from sulfinyl chirality to the prochiral center on the bicyclic ring.

• 公益社団法人日本薬学会の論文
• 1998-05-15

著者

• 今西 武

  大阪大学大学院薬学研究科

• 岩田 宙造

  阪大院薬

• Tanaka T

  Kvushu Univ. Fukuoka Jpn

• Tanaka T

  Osaka Univ. Osaka Jpn

• IWATA Chuzo

  Faculty of Pharmaceutical Sciences, Osaka University

• Iwata Chuzo

  Faculty Of Pharmaceutical Sciences Osaka University

• Tokuno K

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 恒雄

  Department Of Pharmacy Hyogo College Of Medicine

• 高橋 以都美

  Faculty Of Pharmaceutical Sciences Osaka University

• Tanaka Tetsuaki

  Faculty Of Pharmaceutical Sciences Osaka University

• MAEZAKI Naoyoshi

  Faculty of Pharmaceutical Sciences, Osaka University

• Maezaki Naoyoshi

  Faculty Of Pharmaceutical Sciences Osaka University

• Imanishi Takeshi

  Graduate Shool Of Pharmaceutical Sciences Osaka University

• 正垣 武志

  Research Department Sawai Pharmaceutical Co. Ltd.

• Tanaka T

  School Of Pharmaceutical Sciences Nagasaki University

• SHOGAKI Takeshi

  Faculty of Pharmaceutical Sciences, Osaka University

• IMAMURA Tuneaki

  Faculty of Pharmaceutical Sciences, Osaka University

• TOKUNO Katsuya

  Faculty of Pharmaceutical Sciences, Osaka University

• OHKUBO Kazumi

  Faculty of Pharmaceutical Sciences, Osaka University

• TANAKA Tatsuaki

  Faculty of Pharmaceutical Sciences, Osaka University

• Ohkubo K

  Faculty Of Pharmaceutical Sciences Osaka University

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

関連論文

• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. IV.A Stereoselective Formal Total Synthesis of (±)-Aphidicolin
• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. III.An Alternative Stereoselective Access to Aphidicolane-Type B/C/D-Ring System
• 61 アフィディコラン型およびステモダン型ジテルペンの合成研究(ポスター発表の部)
• スカベンジャー受容体ノックアウトマウスを用いたDNAの取り込み機構の解析
• スカベンジャーレセプターのα-ヘリカルコイルドコイルドメインの構造
• Synthesis and Evaluation of Novel Thiazolidine Derivatives as Thromboxane A_2 Receptor Antagonists
• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. II. Neighboring Hydroxyl Group Participation in Stereoselective Syntheses of Tricyclo[6.3.1.0^]dodecanes Corresponding to the B/C/D-Ring Systems
• Synthetic Studies on Spiroketal Natural Products. V. Total Synthesis of (+)-Talaromycin A and (-)-talaromycin B
• Synthetic Studies on Spiroketal Natural Products. IV.A Stereoselective Synthesis of (3S, 5S, 6R, 9R, R_S)-3-Benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro[5.5]undecane, a Key Intermediate for Talaromycins
• Flavonol Glycosides in Leaves of Two Diospyros Species
• 102(P-59) (±)-Scopadulinの全合成(ポスター発表の部)
• NMRによるTCBPのDNA結合ドメインの溶液構造解析
• 131(P-78) 抗腫瘍活性アセトゲニンMosin Bの不斉合成研究(ポスター発表の部)
• 50(P10) Macrocarpal類の不斉合成研究(ポスター発表の部)
• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. V. A Facile Formal Total Synthesis of (±)-Aphidicolin via a Lewis Acid-Mediated Stereoselective Spiroannelation
• Lewis Acid-Mediated Stereoselective Spiroannelation : A Facile Access to Aphidicolane and Stemodane B/C/D Ring Systems
• P-18 (+)-Perhydrohistrionicotoxinの合成(ポスター発表の部)
• Synthetic Studies on Aromadendrane-Type Compounds. II.Stereoselective Synthesis of (+)-1,2-Didehydroaromadendrane
• Synthetic Studies on Aromadendrane-Type Compounds. I. Stereoselective Construction of Aromadendrane- and Alloaromadendrane-Type Skeletons
• Construction of Asymmetric Quaternary Carbon Center Containing Heteroatom via Regioselective Cleavage of Cyclopropane Ring Mediated by Mercury(II) Salt
• Synthetic Study on Gymnomitrol. II. A Synthesis of (±)-Isogymnomitrol
• 57 アロマデンドラン型化合物の不斉合成研究(ポスター発表の部)
• Synthetic Study on Gymnomitrol and Related Compounds. I.Preparation and Cyclopropane Ring Opening of 1,2,6-Trimethyltetracyclo[5.3.1.0^.0]undecan-9-one
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. VI. An Improved Formal Synthesis of (±)-Descarboxyquadrone via Highly Regioselective Cyclopropane Ring Opening of Tricyclo[3.3.0.0^]octan-3-one
• Efficient Chiral Induction by Diene Iron-Tricabonyl Moiety. IV. : Asymmetric Total Synthesis of a Piperidine Alkaloid, SS20846A
• Excellent Chiral Introduction by Diene Iron-Tricarbonyl Moiety. III : Asymmetric Synthesis of Hydroxyethylidene Dipeptide Isostere Using a Diastereoselective 1,2-Nucleophilic Addition of Organocerium Reagents into a 1-Azatriene Fe(CO)_3 Complex
• Excellent Chiral Introduction by Diene Iron-Tricarbonyl Moiety. II : A Formal Synthesis of (+)- and (-)-Frontalin Using a Diastereoselective 1,2-Nucleophilic Addition of Organometallics into a (Z)-Dienone Fe(CO)_3 Complex
• 93(P-22) 抗腫瘍活性アセトゲニン類の系統的不斉合成法の開発 : Murisolinの不斉合成への応用(ポスター発表の部)
• P-448 STRUCTURES OF STILBENE OLIGOMERS IN DIPTEROCARPACEAEOUS PLANTS
• New resveratrol oligomers in the stem bark of Vatica pauciflora
• Differential display法を用いた巨核球への分化誘導刺激に応答する遺伝子の探索
• Synthesis of 7-Thiaprostaglandin E_1 Congeners : Potent Inhibitors of Platelet Aggregation
• Synthesis of Thiaprostaglandin E_1 Derivatives
• SYNTHESIS OF NEW ANTINEOPLASTIC ALKYLIDENECYCLOPENTENONES
• TOTAL SYNTHESES OF STABLE PGI_2 DERIVATIVES : SYNTHESES OF 7-HYDROXY-AND 7-FLUORO-PGI_2
• イソカルバサイクリンメチルエステル含有 O/W エマルジョン製剤 TTC-909 の体内動態 (第4報) 単回静脈内投与後のイヌにおける血中濃度, 排泄および代謝
• イソカルバサイクリンメチルエステル含有 O/W エマルジョン製剤 TTC-909 の体内動態 (第2報) ラットにおける代謝
• Platelet Anti-aggregant Activity of 2,2-Dimethylthiazolidine Hydrochloride and 2-(4-Hydroxy-3-methoxyphenyl)thiazolidine
• A FORMAL TOTAL SYNTHESIS OF (±)-QUADRONE
• Diastereoselective Synthesis of Optically Active C2-Substituted Spiro[4.5]decanes : Two Key Intermediates for Spirovetivane Sesquiterpenes
• Synthetic Studies on Acorane-Alaskane Sesquiterpenes. I. Total Synthesis of (±)-β-Acorenol
• P-53 ジエン鉄カルボニル錯体を不斉発現素子とし用いた不斉合成反応の開発および生理活性物質の不斉合成(ポスター発表の部)
• Melanogenesis Stimulation in Murine B16 Melanoma Cells by Kava (Piper methysticum) Rhizome Extract and Kavalactones(Pharmacognosy)
• Asymmetric Desymmetrization of Prochiral 1,3-Diols via Diastereoselective C-O Bond Fission of Bicyclic Acetal Using a Chiral Sulfoxide as a Chiral Auxiliary
• Nucleotide Sequences of Membrane-Bound Hydrogenase Gene in Alcaligenes hydrogenophilus
• Antibacterial Activity of Stilbene Oligomers against Vancomycin-Resistant Enterococci (VRE) and Methicillin-Resistant Staphylococcus aureus (MRSA) and Their Synergism with Antibiotics
• A Monoterpene Glucoside and Three Megastigmane Glycosides from Juniperus communis var. depressa
• Synthetic Studies on Spirovetivane Phytoalexins. III. : A Total Synthesis of (±)-Lubiminol
• Synthetic Studies on Spirovetivane Phytoalexins. II. : Stereoselective Synthesis of (2RS, 5RS, 6SR, 8RS, 10SR)-6-Hydroxymethyl-8-methoxymethoxy-10-methyl-2-pivaloyloxyspiro[4.5]decane
• Synthetic Studies on Acorane-Alaskane Sesquiterpenes. II. : Total Synthesis of (±)-Acorenone
• 16 Spirovetivane型Phytoalexin類の合成研究 : (±)-Lubiminolおよび(±)-oxylubiminの立体選択的全合成
• Regioselective Functionalization of the Methylene Group Adjacent to Cyclopropyl Sulfide via Mercury(II)-Mediated Regioselective Ring-Opening Reaction
• Asymmetric Cyclopropanation by Reaction of a γ-Chloromethylated Chiral Vinylic Sulfoxide with Allylmagnesium Bromide
• Synthetic Studies on Spirovetivane Phytoalexins. V. : A Stereoselective Total Synthesis of (±)-Oxylubimin
• Synthetic Studies on Spirovetivane Phytoalexins. IV. : A Stereoselective Synthesis of (±)-3-Hydroxysolavetivone
• Resveratrol Tetramers with a C_6-C_3 or a C_1 Unit from Upuna borneensis
• Resveratrol Oligomers and Their O-Glucosides from Cotylelobium lanceolatum
• A New and Known Cytotoxic Aryltetralin-Type Lignans from Stems of Bursera graveolens
• Resveratrol Derivatives from Upuna borneensis
• Three New Trimeric Stilbenes from Gnetum gnemon.
• Six Flavonostilbenes from Gnetum africanum and Gnetum gnemon
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-r-ones as Synthetic Intermediates. V. : An Improved Synthesis of (±)-Pentalenene
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. IV. : A Further Examination of Cyclopropane Ring Opening in the Tricyclo[3.3.0.0^]octan-3-one System
• Synthetic Studies on Spiroketal Natural Producys. III. : Enantioselective Synthesis of 1,6-Dioxaspiro[4.5]decane Compounds
• Inhibition of Preadipocyte Differentiation by Germacranolides from Calea urticifolia in 3T3-L1 Cells
• Antioxidant Activity of Hydroxyflavonoids
• Antiproliferative Effects Associated with Membrane Lipid Interaction of Green Tea Catechins
• Cell Growth Inhibition by Membrane-Active Components in Brownish Scale of Onion
• Growth Inhibition of Stilbenoids in Welwitschiaceae and Gnetaceae through Induction of Apoptosis in Human Leukemia HL60 Cells(Molecular and Cell Biology)
• Stilbenoids with One Epoxy Group from Cotylelobium lanceolatum
• Vaticanol C-Induced Cell Death Is Associated with Inhibition of Pro-Survival Signaling in HL60 Human Leukemia Cell Line
• Stilbenoids from Leaves of Upuna borneensis
• マクロファージスカベンジャー受容体の細胞質ドメインに存在するエンドサイト-シス等に関与する機能配列の探究
• 1,6-Asymmetric Induction by Reductive Acetal Cleavage of a Bicyclic Acetal Using a Sulfinyl Chiral Auxiliary
• 1,6-Asymmetric Induction Utilizing Asymmetric Desymmetrization by Diastereoselective C-O Bond Fission of the 4-Substituted Bicyclic Acetal : Application to a Synthesis of (-)-Frontalin
• 40年間の化学研究生活を振り返って
• フォストリエシンおよび類縁天然物の合成研究
• ゲノム創薬の高機能性基盤素材としての新しいブリッジ型人工核酸BNA (特集/創薬化学創出へのアプローチ)
• 新規RNA型人工核酸
• 実験メソッド&マニュアル RNAi実験UPDATE(第5回)高機能化siRNAによる遺伝子発現抑制--BNAによるsiRNAの機能化
• 37 抗腫瘍性海洋天然物(±)-Spiroxin Cの全合成(口頭発表の部)
• アンチセンス技術のオーバービューとブリッジ型アンチセンス分子 (化学と生物学の接点がつくるNewバイオテクノロジー) -- (遺伝子発現をあやつる)
• 7 抗腫瘍性抗生物質Fostriecin(CI-920)およびその類縁体の全合成(口頭発表の部)
• アンチセンスBNAオリゴヌクレオチドを用いた遺伝子発現抑制
• ポスト・ゲノム時代に向けた新しい遺伝子治療薬の開発研究--アンチセンス・アンチジーン法の実用化に向けて
• NOVEL AND CHIRAL HANTZSCH-TYPE 1,4-DIHYDROPYRIDINES HAVING A p-TOLYLSULFINYL GROUP. SYNTHESIS AND BIOLOGICAL ACTIVITIES AS CALCIUM CHANNEL ANTAGONISTS
• マクロファ-ジとスカベンジャ-レセプタ- (Vascular Biology〔邦文〕)
• Hepatitis C virus core protein binds to a C-terminal region of NS5B RNA polymerase
• Syntheses and Properties of Novel Conformationally Restrained Nucleoside Analogues
• VXFD in the Cytoplasmic Domain of Macrophage Scavenger Receptors Mediates Their Efficient Internalization and Cell-Surface Expression
• Gene Transfer Mediated by YKS-220 Cationic Particles : Convenient and Efficient Gene Delivery Reagent
• Properties of Cationic Liposomes Composed of Cationic Lipid YKS-220 Having an Ester Linkage : Adequate Stability, High Transfection Efficiency, and Low Cytotoxicity
• Synthesis of Several 3-Substituted 2-Trifluoromethylindoles via Mannich Reaction of 2-Trifluoromethylindoles
• Stereospecific 4-Hydrogen Transfer in the Asymmetric Reduction Using(Ss)-3-(p-Tolylsulfinyl)-1, 4-dihydropyridines, NADH Model Compounds
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. III. : Total Synthesis of (±)-Descarboxyquadrone
• NOVEL AND REGIOSELECTIVE LITHIATION OF THE UNSYMMETRICAL HANTZSCH-TYPE 1,4-DIHYDROPYRIDINE BY PARTICIPATION OF THE NEIGHBORING SULFINYL GROUP
• Studies on Novel and Chiral 1,4-Dihydropyridines. I. Synthesis and Conformational Analysis of Novel NADH Model Compounds, N-Substituted (S)-3-(p-Tolylsulfinyl)-1,4-dihydropyridines
• Syntheses of Optically Active 1,4-Dihydropyridines Having a p-Tolylsulfinyl Group and Their Applications
• Efficient α-Alkylation of α-Amino Acids by Means of a Novel Pyridoxal Model Compound
• Novel and artificial RNAs

もっと見る 閉じる

スポンサーリンク