A New Synthesis of Podophyllum Lignans by Weitz' Aminium Salt-induced Free Radical Cycloaddition Reaction of a Doubly Unsaturated Ester
スポンサーリンク
概要
- 論文の詳細を見る
(±)-Isopodophyllotoxin (1e) and related lactones 12,13,14 were synthesized by a biomimetic procedure from the doubly unsaturated esters 11a and 11b by means of an oxidative free radical cycloaddition reaction utilizing a stable cation radical salt, Weitz' aminium salt, in one step. (±)-Isopicropodophyllin (1g), the trans-fused lactones, 12,13,and 16,and the cis-fused lactone 17 were also synthesized from the esters 11c and 11b by the reaction with the same reagent.
- 公益社団法人日本薬学会の論文
- 1995-11-15
著者
-
飛永 精照
Showa College of Pharmaceutical Sciences
-
Takeya T
Showa Pharmaceutical University
-
竹谷 哲也
Showa College of Pharmaceutical Sciences
-
Tobinaga S
Showa Pharmaceutical University
-
荒 義昭
Showa College Of Pharmaceutical Sciences
関連論文
- Annelation Reactions of Enaminones with Ethyl Acetoacetate. Studies on the β-Carbonyl Compouds Connected with the β-Polyketides. XI
- OXYGENATION OF BIPHENYL BY THE REAGENT SYSTEM Fe(MeCN)^_6-H_2O_2-Ac_2O : AN IMPLICATION TO THE MECHANISM IN MAMMALIAN METABOLISM(Communications to the Editor)
- Relationships between Biological Potency and Electronic States of Polychlorinated Dibenzofurans and Polychlorinated Biphenyls
- Solvent Effect in the Oxygenation of cis-Stilbene Catalyzed by Non-porphyrin and Porphyrin Iron Complexes
- Relationship between the Biological Potency of Polychlorinated Dibenzo-p-dioxins and Their Electronic States
- Non-enzymatic Oxygenation of (+)-Camphor Catalyzed by Iron(II) Acetonitrile Solvate
- Oxygenation of Olefinic Hydrocarbons Catalyzed by Iron(II) Acetonitrile Solvate
- Synthesis of Oxazoles by the Reaction of Ketones with Iron(III) Solvates of Nitriles
- A New Combined Oxidizing Reagent System, Fe (CH_3CN)^_6-IO^-_4 : Oxidation of Paraffin Hydrocarbons
- Oxygenation of Aromatic and Aliphatic Hydrocarbons by a New Reagent System, Fe (CH_3CN)^_6-H_2O_2-Ac_2O : An Effective Model Reagent for Mono-oxygenase
- Gas Chromatography of Triterpenes. I. Ursanane, Oleanane, and Lupane Groups
- A NEW AND REACTIVE DIELS-ALDER DIENE, N, N-DIMETHYLAMINO-3-METHYLTHIOBUTADIENE
- Synthesis of Functionalized Indoles by Diels-Alder Reaction Utilizing the Diene Generated by the Alkylation of N-Methyl-3-thioacetylpyrrole
- A New Aromatic Annelation Reaction with Two Synthons, Enaminones and 3-Oxoglutarate. Studies on the β-Carbonyl Compounds Connected with β-Polyketides. VIII
- Sulfur-Assisted Synthesis of Functionalized Carbazoles
- A SPECIES REACTIVE WITH NITRATE ORGANIC SUBSTRATES IS GENERATED BY ANODIC OXIDATION OF REPCHLORATES IN ACETONITRILE
- Nitration of 3-Acylindoles in the Presence of Metal MeCN Solvates and Synthesis of the Antibiotic Alkaloid Chuangxinmycin(Organic,Chemical)
- A Convenient and Mild Dethioacetalization Method Using Fe(bpy)_3(ClO_4)_3・3H_2O
- Application of Iron(III) Complexes, Tris(2,2'-bipyridyl)iron(III) Perchlorate and Some Iron(III) Solvates, for Oxidative Aryl-Aryl Coupling Reactions
- An Easy Two-Synthon Synthesis of a Sweet Dihydroisocoumarin, (±)-Phyllodulcin. Studies on the β-Carbonyl Compounds Connected with β-Polyketides. IX
- Biogenetic-type Synthesis of (±)-Phyllodulcin, a Sweet Principle of Hydrangea serrata SERINGE var. thunbergii SUGIMOTO (Studies on the β-Carbonyl Compounds connected with the β-Polyketides. VI)
- Syntheses and Anti-histaminic and Anti-allergic Activities of Hexahydro-4-hydroxy-1-benzofuran-2-ones
- A General Synthesis of (±)-Dibenzocyclooctadiene Lignans
- A New Synthesis of Indoloquinolizines by Pictet-Spengler Reaction of Tryptamine Type 1,2-Dihydropyridines Utilizing sec-Nitrodienamine
- Synthesis of 2-Substituted 3-Nitro-1,2-dihydropyridines by Heterocyclic Annulation Reactions of a sec-Nitrodienamine with Aldehyde Compounds
- Reactions of A Nitrodienamine with 1-Protected Indolyllithium
- A New and Efficient Snythesis of 2-Methyl-3-nitro-1,2-dihydropyridines by Heterocyclic Annulation Reactions of sec-Nitrodienamines with Acetaldehyde
- The Antagonistic Effects of Khellactones on Platelet-Activating Factor, Histamine, and Leukotriene D_4
- Pharmacological Activities of the Prenylcoumarins, Developed from Folk Usage as a Medicine of Peucedanum japonicum THUNB.
- ANTI-HISTAMINIC AND ANTI-ALLERGIC PRINCIPLES OF PETASITES JAPONICUS MAXIM.
- Synthesis of Anacardic Acids, 6-[8(Z), 11(Z)-Pentadecadienyl]salicylic Acid and 6-[8(Z), 11(Z), 14-Pentadecatrienyl]salicylic Acid
- Improved Synthesis of Anacardic Acids, 6-Pentadecylsalicylic Acid and 6-[8(Z)-Pentadecenyl]salicylic Acid, from Aldehyde and Acetoacetate
- Synthesis of Anacardic Acids Utilizing an Annelation Reaction of Isoxazoles with Ethyl Acetoacetate
- Total Synthesis of Racemic Ligularone and Isoligularone
- Aminoacrylates. II. An Efficient Synthesis of α-Pyridones by Heterocyclic Annelation Reactions of Magnesium Amides Derived from sec-Aminoacrylates with Methyl Propiolate
- Aminodienyl Esters III : A New Synthesis of 1,4-Dihydropyridines by Self-Heterocyclic Annelation Reactions of sec-Aminodienyl Esters
- Aminoenylesters. I. A New Synthesis of 1,2,3,4-Tetrahydropyrimidines by Heterocyclic Annelation Reactions of Aminoenylesters with Primary Amines and Acetaldehyde
- Aminodienylesters. I : The Cycloaddition Reactions of tert-Aminodienylester with α, β-Unsaturated Carbonyl Compounds, Styrenes, and Quinones
- Aminodienylesters. II. A New Synthesis of 2,3-Dihydro-6H-1,3-oxazines by Heterocyclic Annelation Reactions of sec-Aminodienylesters with Acetaldehyde
- Total Synthesis of Dictamnol, a Trinor-Guaiane Type Sesquiterpene from the Roots of Dictamnus dasycarpus TURCZ.
- A New Concise Synthesis of Arcyriacyanin A and Its Unique Inhibitory Activity against a Panel of Human Cancer Cell Line
- Syntheses of Naturally Occurring 5-Carbonylmethyl-7-hydroxy-2-methyl-chromones and -chromanone (Studies on the β-Carbonyl Compounds Connected with the β-Polyketides. X)
- BIPHENYLS, A NEW CLASS OF COMPOUND THAT INHIBITS PLATELET-ACTIVATING FACTORS
- Dictamnol, a New Trinor-Guaiane Type Sesquiterpene, from the Roots of Dictamnus dasycarpus TURCZ.
- Nitrodienamines : An Easy Synthesis and [4+2] Cycloaddition Reactions with α, β-Unsaturated Carbonyl Compounds and Quinones
- Biogenetic-type Synthesis of 3,4-Dihydro-8-hydroxy-3-phenylisocoumarin : Studies on the β-Carbonyl Compounds connected with the β-Polyketides. V
- Intra- and Intermolecular Condensation Reactions of 8-Phenyl-7-octene-2,4,6-trione and 8-Phenyl-2,4,6-octanetrione (Studies on the β-Carbonyl Compounds connected with the β-Polyketides. IV)
- New Synthetic Routes to β-Polyketone Derivatives : Reactions of 3-Acetyl-2-hydroxy-6-methyl-4H-4-pyranone and 7-Chloro-2,2-dimethyl-2H, 4H, 5H-pyrano [4,3-d]-1,3-dioxin-4,5-dione with an Enamine (Studies on the β-Carbonyl Compounds connected with the β-Po
- Total Synthesis of (±)-Plumbazeylanone, A Naphthoquinone Trimer from Plumbago zeylanica
- Total Synthesis of (±)-Plumbazeylanone
- A Synthesis of Arcyriacyanin A, an Unsymmetrically Substituted Indole Pigment of the Slime Mould by Palladium Catalyzed Cross-Coupling Reaction
- Iron(III) Picolinate-Catalyzed Oxidative Demethylation of N, N-Dimethylaniline with Hydrogen Peroxide in the Presence of Acetic Anhydride
- STEREOSELECTIVE 7α-HYDROXYLATION OF 3β-ACETOXY-Δ^5-STEROIDS BY Fe(PA)_3/H_2O_2/MeCN
- Utility of Weitz' Aminium Salt for Obtaining Quinones as Potential Synthetic Precursors of Quassinoids
- Iron(III)Picolinate-Catalyzed Oxygenation of Cholesteryl Acetate with Hydrogen Peroxide or Peracetic Acid
- Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes
- Reactions of 1-Naphthols with π-Acceptor p-Benzoquinones : Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation
- A New Electrochemical System for Stereoselective Allylic Hydroxylation of Cholesteryl Acetate with Dioxygen Induced by Iron Picolinate Complexes
- Iron(III)Picolinate-Induced Oxygenation and Subsequent Rearrangement of Triterpenoid Derivatives with Hydrogen Peroxide
- Biomimetic Synthesis of Podophyllum Lignans
- New Reagent Systems Containing CrO_3 Provide Precursors for Syntheses of Neo-lignans
- A Practical Synthesis of d, l-Dibenzocyclooctadiene Lignans, d, l-Deoxyschizandrin, d, l-Wuweizisu C, and Their Stereoisomers
- Synthesis of a Simple (±)-Dibenzocyclooctadiene Lignan, (±)-Normethylgomisin A
- Synthesis of (±)-Dibenzocyclooctadiene Lignans, (±)-Isoschizandrin, and Their Stereoisomers, Utilizing the Samarium-Barbier Reaction
- Synthesis of Biphenyls by Acid-Catalyzed Condensation Reactions of 1-Oxaspiro[4.5]deca-6,9-diene-2,8-dione with Phenols or Phenol-ethers(Organic,Chemical)
- An Approach for General Synthesis of Biphenyl Neolignans by the Reaction of 1-Oxaspiro[4.5]deca-6,9-diene-2,8-dione with the Grignard Reagent and Synthesis of Magnaldehyde B(Organic,Chemical)
- Synthesis of Unsymmetrical Biphenyl Lignans, Honokiol and Related Compounds, Utilizing Quinol-acetates as Reactive Intermediates
- A Novel Oxidation Product Formed by the Oxidation of Di (1-propenyl)-tetramethoxybiphenyl with CrO_3-HBF_4-MeCN
- A New Synthesis of Podophyllum Lignans by Weitz' Aminium Salt-induced Free Radical Cycloaddition Reaction of a Doubly Unsaturated Ester
- Reactions of Lignan Precursors, Cinnamyl Alcohols and Cinnamic Acids, with Weitz' Aminium Salt
- Synthesis of (±)-Dibenzocyclooctadiene Lignans, (±)-Schizandrin, (±)-Gomisin A and Their Stereoisomers, Utilizing the Samarium-Grignard Reaction