Synthetic Studies on Cephalotaxus Alkaloids. A Synthesis of (±)-Cephalotaxine

スポンサーリンク

概要

• 論文の詳細を見る

• A stereoselective total synthesis of (±)-cephalotaxine (1) has been achieved. Palladium-catalyzed [3+2] cycloaddition of 2-(trimethylsilylmethyl)-2-propenyl acetate to the nitrostyrene 7 gave the methylenecyclopentane 6,which was converted into the α-sulfinylacetamide 19. Treatment of 19 either with trifluoroacetic anhydride in dichloromethane at room temperature or with p-toluenesulfonic acid in boiling 1,2-dichloroethane gave the benzazepinone 20 in good yield, and this was transformed to (±)-1 via Hanaoka's key intermediate 4.

• 社団法人日本薬学会の論文
• 1993-02-15

著者

• 岡野 昌彦

  Kyoto Pharmaceutical University

• 木戸 勝

  Second Institute Of New Drug Research Otsuka Pharmaceutical Co. Ltd.

• 池田 正澄

  Kyoto Pharmaceutical University

• 池田 正澄

  京都薬科大学

• 石橋 弘行

  Kyoto Pharmaceutical University

• 石橋 弘行

  金沢大学薬学部

• 石橋 弘行

  京都薬科大学

• 小阪 圭吾

  Kyoto Pharmaceutical University

• 木戸 勝

  Otsuka Pharmaceutical Co., Ltd.,

• 小坂 圭吾

  Kyoto Pharmaceutical University

• Kido Masaru

  Second Institute Of New Drug Research Otsuka Pharmaceutical Co. Ltd.

関連論文

• Synthesis of Diclofenac
• The Reaction of Vinyl Sulfones with Iodine Azide : Synthesis and Thermal Reactions of β-Azidovinyl Sulfones
• The Crystal Structures of 5-Hydroxy-3,4-dihydro-2-quinolone and 5-Hydroxy-1-methyl-3,4-dihydro-2-quinolone
• The Crystal Structures of 2-Quinolone and 8-Acetoxy-2-quinolone
• The Crystal Structure of Carteolol Hydrochloride : 5-(3-tert-Butylamino-2-hydroxy) propoxy-3,4-dihydro-2-quinolone, OPC-1085
• Syntheses of Arenediacetic Esters and Acetonyl-Substituted Arylacetic Esters by Means of Friedel-Crafts Reaction with α-Acyl-α-chlorosulfides
• Syntheses of Arylacetone and Arylacetonitrile by Friedel-Crafts Reaction with α-Chloro-α-(methylthio)-substituted Acetone and Acetonitrile
• Synthesis of the Erythrinan Skeleton by Acid-Promoted Cyclization of N-(3-Oxo-1-cyclohexen-1-yl)-N-[2-(3,4-dimethoxyphenyl) ethyl]-α-(methylsulfinyl) acetamide
• Reaction of Benzo [b] furan and 1-Acylindoles with Iodine Azide
• Synthesis and Some Chemical Transformations of 2-Azidomethylindoles
• Synthesis and Thermolysis of 3-Azidoindolenines
• Ring Expansion Reaction of 2,2-Dimethyl-2,3-dihydrobenzo [b]-thiophene N-(p-Toluenesulfonyl) sulfilimine
• α-クロロスルフィドを用いる炭素-炭素結合形成反応の最近の進歩
• 硫黄原子に隣接する炭素陽イオンを用いる炭素-炭素結合形成反応の開発とその利用に関する研究
• Stereochemisty of 1,3-Dipolar Cycloadditions of Nitrones with (E)-1-Alkyl-2-nitroethenes
• ラジカル環化反応の位置化学の制御と生理活性化合物合成への応用
• 学術振興賞受賞 向 智里氏の業績
• カルバモイルメチルラジカルの環化反応と天然物合成への応用
• Convenient Synthesis of 4-Alkyl, Alkenyl, and Alkynyl Substituted N-(Phenylsulfonyl)indoles
• New, Concise Route to Indoles Bearing Oxygen or Sulfur Substituent at the 4-Position. Synthesis of (±)- and (S)-(-)-Pindolol and (±)-Chuangxinmycin
• Synthetic Studies on Cephalotaxus Alkaloids. A Synthesis of (±)-Cephalotaxine
• Carbamoylmethl Radical Cyclization : Formal Synthesis of (-)-Trachelanthamidine
• Synthesis of (±)-D-Homocephalotaxine, an Unnatural Analogue of Cephalotaxine
• Synthesis of ortho-Substituted Arylacetic Esters and Related Compounds by Means of Sommelet-Hauser Rearrangement of Sulfur Ylides
• Synthesis of Unsymmetrically Substituted Benzils via the Friendel-Crafts Reaction of Arenes with α-Chloro-α-(methylthio)acetophenones
• Lewis Acid-Promoted Alkylations of Arenes and 1-Trimethylsilylalkynes with β-Chloro-β-thiopropanoic Esters
• New Entries to 2(1H)-Quinolinones and 2H-1-Benzazepin-2-ones by Acid-Catalyzed Olefin Cyclization of N-[o-(Alk-1-enyl)phenyl]-2-(methylsulfinyl)acetamides
• Synthesis of (±)-β-Cuparenone Based on a Lewis Acid-Promoted [4^++2] Polar Cycloaddition of m-Tolylthiomethyl Chloride
• Synthesis of Thiochromans by Means of a [4^++2] Polar Cycloaddition of m-Tolylthiomethyl Chloride with Substituted Alkenes : A Simple Synthesis of (±)-Cuparene and Related Sesquiterpenoids
• A Concise Total Synthesis of (±)-3-Demethoxyerythratidinone Based on an Acid-Promoted Double Cyclization of α-Sulfinylacetamides
• Synthesis of α-(Methylthio)arylacetamides and Their Conversion into Some Biologically Active Arylethylamines
• A New, Convenient Route to Erbstatin and N-Acetyl-1,2-didehydrodopamine
• A Convenient Synthesis of 1,3,4,5,-Tetrahydro-2H-3-benzazepin-2-ones by Acid-Catalyzed Cylization of N-(2-Arylethyl)-N-methyl-2-sulfinylacetamides
• 硫黄原子に隣接する炭素陽イオンを用いる炭素-炭素結合形成反応の新しい展開
• Photochemistry of 2-(N-Acyl-N-alkylamino)cyclohex-2-enones : Formation of Spiro-β-lactams(Organic,Chemical)
• Synthesis of 2(1H)-Quinolinone Derivatives and Their Inhibitory Activity on the Release of 12(S)-Hydroxyeicosatetraenoic Acid (12-HETE) from Platelets
• Stereochemistry of Alkylation of Cyclic β-Ketosulfoxides. III. Alkylation and Deuteration of the Dianion of Isothiochroman-4-one 2-Oxide
• Stereochemistry of Alkylation of Cyclic β-Ketosulfoxides. II. Alkylations of 2-Methylbenzo [b] thiophen-3 (2H)-one 1-Oxide
• Stereochemistry of Alkylation of Cyclic β-Ketosulfoxides. I. Alkylations of 3-Methylisothiochroman-4-one 2-Oxide and 2-Methylthian-3-one 1-Oxide
• Reaction of the α, α'-Dianion of β-Ketosulfoxide
• Synthesis of Ethyl Arylacetates by Means of Friedel-Crafts Reaction of Aromatic Compounds with Ethyl α-Chloro-α-(methylthio) acetate
• Olefin Cyclization Initiated by α-Thiocarbocation : A Novel Route to Pyrrolizidine Alkaloids
• 30 沖縄サンゴ礁生物Clavularia属軟サンゴ2種の成分研究
• Marine Natural Products. XII. On the Chemical Constituents of the Okinawan Marine Sponge Hymeniacidon aldis
• CLAVUKERIN A, A NEW TRINOR-GUAIANE SESQUITERPENE FROM THE OKINAWAN SOFT CORAL CLAVULARIA KOELLIKERI
• THREE NEW ent-VALERENANE SESQUITERPENES FROM AN OKINAWAN SOFT CORAL
• Absolute Structure of Ionol Glucoside : A Single-Crystal X-Ray Analysis of Dendranthemoside A Pentaacetate
• Conformation and Absolute Sterochemistry of Macrocalyxoformin D (=Longirabdiol)
• A Practical Synthesis of (S)-(-)-Nadifloxacin : Novel Acid-Catalyzed Racemization of Tetrahydroquinaldine Derivative
• Synthesis of 5-Fluorouracil Derivatives Containing an Inhibitor of 5-Fluorouracil Degradation
• Stichlorogenol and Dehydrostichlorogenol, Genuine Aglycones of Stichlorosides A_1,B_1,C_1 and A_2,B_2,C_2,from the Sea Cucumber Stichopus Chloronotus (BRANDT)
• Reactions of 1-Methyl-1H-1,2,4-triazolium 4-Imine and 4-Acylimines with Acetylenic Esters
• Synthesis of (±)-endo- and (±)-exo-Brevicomin via Ene Reaction of the Pummerer Rearrangement Product Derived from 4-ChIorophenyl Methyl Sulfoxide(Organic,Chemical)
• Reaction of 2-Methyl-4-phenyl-2,3-dihydro-1H-pyrazolo[2,3,4-de][1,5]-naphthyridine 2-Oxides with Acetic Anhydrides : Polonovski Reaction versus Mesomeric Betaine Formation
• 新反応を求めて : 含窒素複素環化合物の合成研究を中心に
• 私学における教育と研究
• ラジカル環化反応における位置及び立体化学の制御と天然物合成
• 5-Endo-trig型ラジカル環化反応
• Synthesis and Some Properties of 2-Azathiabenzene 1-Oxides
• Nucleophilic Reactions of N-Unsubstituted Sulfoximines with Activated Acetylenes, Olefins, and Diphenylcyclopropenone
• Synthesis and Absolute Configuration of the Enantiomers of 7-Fluoro-1-methyl-3-(methylsulfinyl)-4(1H)-quinolinone (Flosequinan)
• 1,3-Dipolar Cycloaddition Reaction of 1-Methylperimidine 3-Ylides with Dimethyl Acetylenedicarboxylate
• Photochemical Syntheses of 2-Heterobicyclo-[3.2.0] heptane and-[4.2.0] octane Ring Systems
• The Absolute Configuration of (R)-(+)-Nadifloxacin
• Cationic Polar Cycloadditions of Phenylthionium Ions with Olefins : A New Route to Thiochromans
• Crystal Structures of Nadifloxacin Anhydride and Its Hemihydrate
• X-Ray Structures of Two Photodimers of 2-Methyl-1,4-naphthoquinone (Menadione)
• Intramolecular [2+2] Photocycloaddition of 2-[N-Acyl-N-(2-propenyl)-amino] cyclohex-2-enones : Synthesis of 2-Azabicyclo [2.1.1] hexanes
• INTRAMOLECULAR PHOTO [2+2] CYCLOADDITION OF 2-ALLYLOXY-AND 2-ALLYLAMINOCYCLOHEX-2-ENONES : FORMATION OF 2-OXA-AND 2-AZA-BICYCLO [2.1.1] HEXANE SYSTEMS
• O-Arenesulfonyl-N-alkylhydroxylamines as Aminating Reagents
• Photolysis and Thermolysis of 3-Diazothiochroman-4-one and Related Compounds
• Synthesis, Stereochemistry, and Rearrangement of N-Tosylsulfilimines and (Bismethoxycarbonyl) methylides of 1,4-Dimethylthioxanthene and Its 9-Alkyl Derivatives
• Monomethylation of Aromatic Rings by Friedel-Crafts Reaction with Chloromethyl Sulfide
• 1-アシルー1-チオカルボカチオンを用いる合成反応
• The Photorearrangement and Thermolysis of N-Benzoyliminoisoquinolinium and Quinolinium Betaines
• Intramolecular Photo [2+2] cycloaddition of 2-Alkenoyloxycyclohex-2-enones
• Glochidionolactones A-F : Butenolide Glucosides from Leaves of Glochidion zeylanicum (GAERTN) A. JUSS
• A Novel Dimeric Butenolide, Glochidiolide, from the Leaves of Glochidion Acuminatum MUELL
• 硫黄原子に隣接する炭素陽イオンを用いる 炭素一炭素結合形成反応の新しい展開
• 1-アシル-1-チオカルボカチオンを用いる合成反応
• Polonovski反応の合成化学への応用
• ヘテロ芳香族N-イミンの化学 (ヘテロ環の化学)
• 3-ハロインドレニンの化学
• ラジカル環化反応の位置化学の制御と生理活性化合物合成への応用

もっと見る 閉じる

スポンサーリンク