新規有機合成の開発を基盤とする抗腫瘍活性天然物ならびに創薬先導化合物の合成研究
スポンサーリンク
概要
- 論文の詳細を見る
Biologically active natural products with unique, highly complex molecular skeletons have been used as leading compounds for raw materials of new drugs. Due to the limitations of natural supply, highly efficient, large-scale syntheses and molecular design have been sought in drug discovery. For this purpose, we have focused on a synthetic strategy effective in developing novel reactions and reagents and found several useful regio- and stereospecific reactions, contributing to the synthesis of otherwise unattainable target molecules. The application of these reactions for the total synthesis of three types of potent cytotoxic natural products for the first time is described in this paper. The basic concept is first described. Then the total synthesis of anthracyclines, fredericamycin A, and discorhabdins is reported. Novel reactions using hypervalent iodine reagents under environmentally benign conditions are also described. The future prospects for this method are discussed.
- 社団法人日本薬学会の論文
- 2002-12-01
著者
-
北 泰行
大阪大学大学院薬学研究科
-
北 泰行
大阪大学薬学部
-
Kita Yasuyuki
Graduate School Of Pharmaceutical Sciences Osaka University Yamadaoka
関連論文
- 光学活性アセタール類を利用する遠隔位不斉誘導反応の開発と天然物不斉合成への応用
- リパーゼの不斉識別能を活用する新規不斉合成反応の開発研究
- Synthesis of 2-(Heteroarylthiomethyl)-1β-methylcarbapenem via Propargylation of 4-Acetoxy-2-azetidinone with 3-Methyl-1-tributylstannylallene
- Hypervalent Iodine Oxidation of Ethynylcarbinols : A Short and Efficient Conversion of Dihydroxyacetonyl Groups from Keto Groups
- Hypervalent Iodine Oxidation of α,β-Unsaturated Carbonyl Compounds(Organic,Chemical)
- 超原子価ヨウ素の化学の新展開とグリーンケミストリー (特集 未来社会を支える化学技術)
- 今こそチャレンジの時
- リパーゼが触媒する不斉合成反応の新展開
- Hypervalent Iodine(III) Reagent-Promoted Rearrangement and Subsequent Oxidative Ring Cleavage of Cyclic 2,3-Epoxy-1-alcohol Derivatives
- ディスコハブディン類の合成:超原子価ヨウ素化合物の反応 (最新有機合成化学--ヘテロ原子・遷移金属化合物を用いる合成) -- (第3部 天然物合成)
- 超原子価ヨウ素試薬を用いる水中での新規酸化反応の開発
- 新規基盤反応開発と抗腫瘍活性天然物の全合成 (特集 天然物化学の技術進歩)
- 学術振興賞受賞 赤井周司氏の業績
- 電子求引性保護基(アシル基, スルホニル基)を持つエポキシアルコール類の酸転位反応 : 不斉四級炭素および不斉スピロ中心の構築と天然物合成への応用
- グリーンケミストリーを指向したラジカル開始剤 (特集 ファインケミカルにおけるラジカル反応--グリーンケミストリーをめざして)
- 新規有機合成の開発を基盤とする抗腫瘍活性天然物ならびに創薬先導化合物の合成研究
- 超原子価ヨウ素試薬を用いるフェノール類の酸化的カップリング反応の開発とAmaryllidaceae Alkaloids合成への応用
- 奨励賞受賞 当麻博文氏の業績
- フレデリカマイシンAの全合成 (生物活性天然物の合成--複雑な構造をいかにして構築するか) -- (天然物の合成)
- 田村恭光先生を偲んで
- Hypervalent Iodine(III)-induced Intramolecular Cyclization Reaction of Substituted Phenol Ethers with an Alkyl Azido Side-chain : A Novel and Efficient Synthesis of Quinone Imine Derivatives
- 化学的不斉非対称化法はすでに酵素法を越えたか?--σ対称ジオール類の高立体選択的な不斉非対称化 (1999年の化学(4))
- Studies on Asymmetric Total Synthesis of Antitumor Antibiotic, Fredericamycin A
- プメラー反応の新展開
- 日本薬学会奨励賞受賞 本多利雄氏の業績
- シリル化試薬
- 第6回反応と合成の進歩シンポジウム
- P-194 Preparation of Optically Active Allyl Acetates by Lipase-Catalyzed Dynamic Kinetic Resolution
- An Efficient p-Thiocyanation of Phenols and Naphtols Using a Reagent combination of Phenyliodine Dichloride and Lead(II) Thiocyanate
- キラル保護基--キラルアセタ-ルおよびキラルアセタ-ル型保護基 (金属反応剤を用いる不斉化学合成) -- (金属の複合的な利用法)
- ORGANIC SYNTHESIS UTILIZING BECKMANN FRAGMENTATION : ASYMMETRIC CARBON-CARBON BOND FORMATION VIA CHIRAL ACETAL INTERMEDIATES
- Asymmetric Synthesis of Anthracyclinones : Synthesis of a New Chiral AB-Synthon, (5R, 6R)-6-Ethyl-5,6-dihydroxy-5,6,7,8-tetrahydro-1,4-naphthoquinone, and Its Application for a Novel Regioselective Synthesis of (-)-γ-Rhodomycinone
- Asymmetric Synthesis of Anthracyclinones : Regio- and Stereoselective Synthesis of (-)-7-Deoxydaunomycinone through Direct Asymmetric Introduction of an Alkynyl Unit into C9 Ketone
- Asymmetric Synthesis Using Chiral Acetals : Highly Stereoselective Reduction of Chiral α-Keto-β, γ-unsaturated Acetals and Its Application for the Synthesis of (R)-(-)- and (S)-(+)-3'-Methoxy-4'-O-methyljoubertiamine
- Asymmetric Synthesis Using Chiral Acetals : Highly Diastereoselective Nucleophilic Addition of Grignard Reagents to Chiral 1-Oxo-β-tetralone 1-Acetals
- Asymmetric Synthesis Using Chiral Acetals : Highly Diastereoselective Addition of Organocerium Reagents to Chiral α-Aldoxime-Ether Acetal
- Lipase-Catalyzed Asymmetric Desymmetrization of Prochiral 2,2-Disubstituted 1,3-Propanediols Using 1-Ethoxyvinyl Benzoate
- Reaction of Silylketenes with Carbanions : Simple Preparation of α-Silylketones Using Organocerium Reagents
- Chemistry of Silylketenes : Simple Preparation of Silylallenes by the Reaction of Silyketenes with Phosphorus Ylides
- Synthetic Anthracyclines : Total Synthesis of D-Ring Pyridine and Pyrazine Analogues of 11-Deoxydaunomycin
- Synthetic Anthracyclines : Regiospecific Total Synthesis so D-Ring Thiophene Analogues of Daunomycin
- Total Synthesis of 11-Deoxyanthracyclines : 4-Demethoxy-11-deoxy-daunomycin : 11-Deoxydaunomycin, and Their Analogues
- An Efficient, Regiospecific Synthesis of 4-Demethoxydaunomycinone and Daunomycinone(Organic,Chemical)
- A Novel Oxidative Intramolecular [4+2]Cycloaddition of Silylene-Protected Dihydroxystyrene Derivatives Leading to peri-Hydroxy Polycyclic Aromatic Compounds : A Synthesis of the ABCD Ring System of Frederucamycin A
- Strong Base-Induced Cycloaddition Reaction of Homophthalic Anhydride with Aldehydes
- Synthetic Anthracyclines : Regiospecific Total Synthesis of a D-Ring Indole Analogue of Daunomycin
- Photochemical and Thermal Behavior of 2-Benzoyl-3-ethoxycarbonyl-methylcyclohex-2-enone and Its Derivatives
- Chemistry of O-Silylated Ketene Acetals : A Stereoselective Synthesis of Optically Active Carbapenem Antibiotics, (+)-Thienamycin and (+)-PS-5
- Chemistry of O-Silylated Ketene Acetals : A Mild and Convenient Synthesis of β-Lactam Antibiotics
- Chemistry of O-Silylated Ketene Acetals : : A Novel Intramolecular Pummerer-Type Reaction of ω-Carbamoylsulfoxide Leading to α-Thiolactams
- Chemistly of O-Silylated Ketene Acetals : Stereocontrolled Synthesis of 3-Benzoylamino-2,3-dideoxy-pentoses by a 1,3-Addition to Chiral Nitrones
- The Chemistry of O-Silylated Ketene Acetals : Synthesis of N-Benzoyl-L-daunosamine
- Chemistry of O-Silylated Ketene Acetals. Novel Chemical Transformation of Vinyl Sulfoxides and Related Sulfoxides(Organic,Chemical)
- Structure of K2O-B2O3 Glasses and Melts (特集 New Trends in Molten Salt Chemistry and Electrochemistry)
- Chemistry of O-Silylated Ketene Acetals : Preparation of α-Siloxy Phenyl Sulfides and Methyl 3-(Phenylthio) butyrates from Alkyl Phenyl Sulfoxides
- Enantioselective Additive Pummerer-Type Rraction in Chiral, Non-racemic Vinyl Sulfoxides Induced by O-Silylated Ketene Acetal
- An Efficient Synthesis of 4-Heterofunction-Substituted 3-(1-Hydroxy)ethylazetidin-2-ones from 3-(1-Hydroxy)ethyl-4-phenylsulfinylazatidin-2-one by Reaction with Silylated Heteronucleophiles
- A Novel Method for the Alkoxylation of Azetidin-2-ones at the 4-Position
- Synthesis of 8-Methoxy-and 8-Methoxy-6-methylhomophthalic Anhydrides, Key Intermediates for the Synthesis of Anthracyclinones and peri-Hydroxylated Polycyclic Aromatic Compounds
- Linearly Condensed peri-Hydroxy Aromatic Compounds Derived from the Cycloaddition Reaction of Homophthalic Anhydrides with Dienophiles
- Rections of 2-Benzoyl-3-chloro-2-cyclohexen-1-ones with Some Organometallic Compounds
- Photochemical Dealkylation of 2-Acyl-3-alkylamino-5,5-dimethyl-2-cyclohexen-1-ones
- Mild and Facile Cleavage of 2-Cyanoethyl Ester Using Sodium Sulfide or Tetrabutylammonium Fluoride. Synthesis of 1,4-Dihydropyridine Monocarboxylic Acids and Unsymmetrical 1,4-Dihydropyridine Dicarboxylates
- Protecting Group for Carboxyl Function : Mild and Facile Cleavage of 2-Cyanoethyl Ester under Non-hydrolytic Conditions
- 光学活性スピロ化合物の新構築 : 抗腫瘍活性天然物の全合成
- Small-angle Neutron Scattering Measurements on SnO_2 Particles Suspended in Liquid Sn-S Systems
- シリルケテンアセタ-ルを用いる不斉Pummerer型反応
- 超原子価ヨウ素化合物を用いる有機合成
- The Improved Synthesis of OPC-29030, a Platelet Adhesion Inhibitor via Diastereoselective Oxidation of Chiral Non-racemic Sulfide
- A Simple Determination Method of the Absolute Configuration of 1-Arylethanthiols by an Intramolecular CH/π Shielding Effect in ^1H-NMR of Diastereomeric Thiol Esters
- Stereospecific Epoxidation of cis-2-Butene-1,4-diones to cis-2,3-Epoxybutane-1,4-diones with Oxodiperoxomolybdenum (VI), MoO_5・H_2O・HMPA
- 学術振興賞受賞 柴田哲男氏の業績
- Cycloaddition to 1,3-Dialkoxycarbonylallenes : One-Step Synthesis of Heterocyclic Compounds Containing a Dialkyl Glutaconate Structure
- アントラサイクリン系抗生物質の合成研究 : ホモフタル酸無水物および関連化合物の環化付加反応
- 制ガン性ペリヒドロキシ芳香族化合物の合成法の開発
- シリルケテンアセタールを用いる不斉Pummerer型反応
- エノ-ル-ケト変換反応を利用したケテンアセタ-ル誘導体のアシル基及びシリル基トランスファ-反応の開発とその天然物合成への応用
- シリルケテンアセタールを用いる有機合成反応
- Reaction of Heteroaromatic Analogs of Homophthalic Anhydride : Synthesis of Hetero Analogs of peri-Hydroxy Polycyclic Aromatic Compounds, Isocoumarins, Isoquinolinones, and Related Compounds
- Synthetic Application of Lithiation Reactions : A Convenient Synthesis of 3,4-Dihydro-5-hydroxycarbostyril, 1,2,3,4-Tetrahydro-5-hydroxy-2-oxo-1,7-naphthyridine, and Methyl 3-Methoxypyridine-4-carboxylate
- 新しいジエンを用いたDiels-Alder反応
- 新組み合わせ試薬トリフェニルホスフィン-チオシアノーゲン (TPPT)