新反応設計と創薬合成への展開

スポンサーリンク

概要

• 論文の詳細を見る

• This review summarizes selected 5 researches fitted to the present title : 1) the synthesis of 1α-hydroxyvitamin D_3,2) the synthesis of cis-2-cyclopentene-1,4-diol, 3) the photochemical methods for the cyclobutane annelation to heteroaromatic compounds and for β-lactam synthesis, 4) the novel total synthetic method of modified nucleosides (e.g. C-nucleoside, N-nucleoside, and their carbocyclic derivatives) and its application to the synthesis of (-)-BCA [1R, 4S, 5R-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine] having anti-HIV activity, and 5) the creation of chiral 1,3-dihetero six-membered ring compounds as novel synthetic intermediates for enantiomerically pure compounds. All the mothods described are practicable (e.g. easy to handle, applicable to large scale preparation, and wide applicability). Among researches 4 and 5,the followings are notable achivements. For 4,BCA is the first nucleoside analog having non-natural sugar moiety. The use of di-l-menthylacetoxymethylenemalonates as dienophiles has offered new cooperative concept in asymmetric Diels-Alder reactions. Reductive retrograde aldol reaction and sodium borohydride-mediated amide bond cleavage reactions developed in this study have been shown to have wide applicability. For 5,several chiral dihetero six-membered compounds (e.g. 1,3-dioxin-4-ones, 1,3-dioxane-4,6-diones, and 1,3-oxazine-4,6-diones) have been synthesized and used successfully for the synthesis of a variety of biologically active compounds (e.g. iridoids, Corey lactone, carbocyclic C-nucleoside, etc.). New proposal involving n-σ^* interaction has been put forward to account for the boat conformation of 1,3-oxazine-4,6-diones.

• 公益社団法人日本薬学会の論文
• 1993-09-25

著者

• 金子 主税

  東北大学

• 金子 主税

  東北大学薬学部

関連論文

• Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
• Cycloadditions in Syntheses. XXXVII. : Syntheses of 6-Trifluoromethyl-1,2,4-triazines and -1,2,4-triazin-5-ones and Their Pericyclic Reactions with Olefins
• Cycloadditions in Syntheses. XXXI. 2+2 Photocycloaddition of 3-Trifluoromethyl Derivatives of Quinoxalin-2(1H)-one and 1,4-Benzoxazin-2-one to Olefins : Effects of the Trifluoromethyl Group(Organic,Chemical)
• DOUBTS ABOUT THE LIBIT'S METHOD FOR THE SYNTHESIS OF THE "COREY"INTERMEDIATE USING PHOTOCYCLOADDITION AS A KEY STEP
• REACTION OF METHANE WITH MOLECULAR FLUORINE : AN AB INITIO MO STUDY
• 学術貢献賞受賞 津田喜典氏の業績
• メディシナル・ケミストリーの新しい流れ
• Addition of Molecular Fluorine to Azlactones : General Synthetic Method of erythro-β-Fluorinated α-Amino Acids
• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines : Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst
• Facile Synthesis of 5α-Fluorocholestan-3-one from 4-Cholesten-3-one via Molecular Fluorine Addition and Reductive Defluorination
• Use of 1,3-Dioxin-4-ones and Related Compounds in Sythesis. XXXVIII. Use of 1,3-Dioxin-4-ones Having a Fluorine or Trifluoromethyl Group at the 5-Position as _π2 Components in [2+2]-Photocycloaddition and Diels-Alder Reactions
• l-MENTHYL (2S)-2-PHENYL-3-(p-ANISYL)-(5Z)-BENZYLIDENE-4,6-DIOXO-1,3-OXAZINE-2-CARBOXYLATE : A NEW CHIRAL HETERODIENE AND MICHAEL ACCEPTOR
• Synthesis of Nucleosides and Their Related Compounds. XII. : Menthyl 2,4-Dioxo-1,3-oxazine-5-carboxylates : New Dienophiles for the Asymmetric Diels-Alder Reaction Directed towards Synthesis of Carbocyclic C-Nucleosides
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis.XVI. : 4-Oxo-1,3-dioxin-5-carboxylic Acids and Related Compounds : Versatile Synthetic Intermediates for the Synthesis of 6-Unsubstituted Six-Membered Heterocyclic Compunds
• 新しい反応活性種,ニトロソケテンを経る機能性環状ニトロンの生成と変型アミノ酸合成への展開
• SELECTIVE PROTECTION OF THE PRIMARY HYDROXYL GROUPS OF OXETANOCIN A AND CONFORMATIONAL ANALYSIS OF O-PROTECTED OXETANOCIN A
• 新規ヌクレオシド分子の構築--炭素環ヌクレオシドを中心に(新規合成法の開発) (核酸化学の新展開--新しい機能性分子を求めて) -- (新しい構造と機能を有するヌクレオシドの分子設計)
• EXPLANATION FOR STEREOSELECTIVITY OF THS CIS-DIHYDROXYLATION OF CIS-3,5-DISUBSTITUTED CYCLOPENTENES
• Synthesis of Nucleosides and Related Compounds. XXXIV. Synthesis of 5-Isonitroso-1,3-dioxane-4,6-diones and Their Reactions
• Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4,t-5-Bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase
• Synthesis of Nucleosides and Related Compounds. XXVI. The Difference in Effects between High Pressure and LiClO_4 for the Diels-Alder Reaction of Cyclopentadiene with Methylenemalonates or O-Acetylisonitrosomalonates
• The Alkylation of 6-Chloropurine with Alcohols by Mitsunobu Reaction
• Synthesis of Nucleosides and Related Compounds. XXII. Carbocyclic Analogues of Thymidine and Related compounds from 2-Azabicyclo[2.2.1]hept-5-en-3-ones
• 超高圧下の有機反応
• Synthesis of Carbocyclic Nucleosides from 2-Azabicyclo[2.2.1]hept-5-en-3-ones : Sodium Borohydride-Mediated Carbon : Nitrogen Bond Cleavage of Five- and Six-Membered Lactams
• Synthesis of Nucleosides and Related Compounds. XVII. Dialkyl 1,3-Dithiethan- and 1,3-Dithiolan-2-ylidenemalonate S-Oxides : Equivalents to Dialkoxycarbonylketenes
• SYNTHESIS OF 9-(t-2,c-3-DIHYDROXYMETHYL-r-1-CYCLOPROPYL)-9H-ADENINE (A LOWER METHYLENE HOMOLOG OF CARBOCYCLIC OXETANOCIN) AND RELATED COMPOUNDS
• HIGHLY STEREOSELECTIVE SYNTHESIS OF CARBOCYCLIC ANALOGUES OF OXETANOCIN
• Synthesis of Nucleosides and Related Compounds. XIV. : Diels-Alder Reaction of Di-l-menthyl Acetoxymethylenemalonate with Cyclopentadiene : Effects of High-Pressure and Catalysts upon Asymmetric Induction
• Titanium Tetrachloride-Mediated Diels-Alder Reactions of Cyclopentadiene with Di-l-menthyl Methylenemalonate and Its Acetoxy Derivative as New Chiral Dienophiles for Asymmetric Induction
• 炭素-炭素二重結合(特にエノン類)への分子フッ素の付加反応
• 分子フッ素を用いたフッ素化反応と含フッ素生理活性物質合成への応用
• 薬学会賞受賞福本圭一郎氏の業績
• 新反応設計と創薬合成への展開
• "知識は真実ではない"ということ
• SYNTHESIS OF 4-TRIFLUOROMETHYLAZETIDIN-2-ONES BY A NOVEL 2+2 PHOTOCYCLOADDITION OF 3-TRIFLUOROMETHYL-QUINOXALIN-2-ONE OR-1,4-BENZOXAZIN-2-ONE TO KETENE
• Novel Annelation Method to Pyridine and Isoquinoline by Photochemical Means
• Photochemical [2+2] Cycloreversion Reactions of 1,2,2a, 8b-Tetrahydrocyclobuta [c] isoquinolin-4 (3H)-ones
• ノルボルネンはなぜ選択的にエキソ面で反応を起こすのか (1992年の化学-11-)
• 化学反応の立体選択性は何によって決まるか-2-反結合性軌道の役割
• 化学反応の立体選択性は何によって決まるか-1-反結合性軌道の役割
• FACILE SYNTHESIS OF THE CARBOCYCLIC ANALOGUE OF β-RIBOFURANOSYL-MALONATE, NEW SYNTHON FOR CARBOCYCLIC C-NUCLEOSIDE FORMATION BY RETROGRADE ALDOL C-C BOND FISSION
• 光化学的周辺環状反応を用いる生理活性化合物の合成

もっと見る 閉じる

スポンサーリンク