Iodine (III)-Mediated Intramolecular Cyclization of Hydroxy Allylsilanes : Synthesis of 5- or 6-Membered β-Methylene Cyclic Ethers

スポンサーリンク

概要

• 論文の詳細を見る

• Oxidative cyclization of hydroxy allylsilanes utilizing the combination of a hypervalent organoiodine compound and a Lewis acid was studied. The allylsilanes 4,prepared from the γ-lactones 1 via conversion to the bis (trimethylsilylmethyl) carbinols 3,on treatment with iodosyl-benzene in the presence of boron trifluoride-etherate in an ethereal solution, afforded the 6-membered β-methylene cyclic ethers 13a and 13b in good yields. Similar treatment of the allylsilanes 8a and 8b gave the 5-membered cyclic ethers 13a and 13b. On the other hand, oxidative cyclization of the carboxylic acid 12 gave a poor yield of the lactone 21 and the major product was found to be the rearranged γ-keto acid 22. Regioselectivity in the iodine (III)-mediated cyclization of 8a is discussed.

• 公益社団法人日本薬学会の論文
• 1985-03-25

著者

• 山口 秀夫

  Osaka University of Pharmaceutical Sciences

• 藤田 榮一

  Osaka University of Pharmaceutical Sciences

• 落合 正仁

  Institute for Chemical Research, Kyoto University

• 藤田 栄一

  京都大学化学研究所

• 藤田 栄一

  Osaka University Of Pharmaceutical Sciences

• 有本 正生

  Osaka College of Pharmacy

• 藤田 榮一

  Institute for Chemical Research, Kyoto University

• 有本 正生

  大阪薬大

• 落合 正仁

  Institute For Chemical Research Kyoto University

• 落合 正仁

  徳島大学大学院ヘルスバイオサイエンス研究部精密薬品製造学分野

• 有本 正生

  Osaka University Of Pharmaceutical Sciences

• 落合 正仁

  京都大学化学研究所

関連論文

• Antitumor Agents. II : Regio- and Stereospecific Syntheses of 1-β-Alkyl-1-desoxypodophyllotoxin Derivatives and Biological Activity
• Antitumor Agents. I. DNA Topoisomerase II Inhibitory Activity and the Structural Relationship of Podophyllotoxin Derivatives as Antitumor Agents
• The Biological Activities of Podophyllotoxin Compounds
• RADIOSENSITIZING HYPOXIC CELLS WITH NEW 3-NITRO-1,2,4-TRIAZOLE DERIVATIVES IN VITRO AND IN VIVO
• クロバナヒキオコシIsodon trichocarpus KUDOの生長にともなう各主ジテルペノイド成分の量的変化そのGC, GC-MSによる検討
• Monitored Aminolysis of 3-Acyl-1,3-thiazolidine-2-thiones : Synthesis of Amides and Amide Alkaloids
• 73 非環状アミドアルカロイドならびに大環状ラクタムアルカロイドの新合成研究
• 34 α-Oxo-methylene類の新酸化反応-その生物活性天然物ならびにモデル化合物合成への応用
• Terpenoids(第31報)Isodon属植物ジテルペノイドのBiogenesisにもとづく分類
• 16 ツルニガクサTeucrium viscidum var. Miquelianumのノルジテルペンについて
• Terpenoids. XXIV. Isolation of Isodonal and Epinodosin from Isodon japonicus and Structure Elucidation of Sodoponin and Epinodosinol, Novel Diterpenoids of the Same Plant
• Terpenoids. XXI. The Structure and Stereochemistry of Isodotricin, a Diterpenoid of Isodon trichocarpus and I. japonicus
• 20 Enmeinの全合成
• 38 Enmein全合成へのapproach
• Terpenoids. XVII. Chemical Conversion of Trichokaurin into Isodocarpin via a Direct Pathway
• Terpenoids(第13報) : Enmeinから誘導される各種立体異性体の薄層クロマトグラフィー
• クロバナヒキオコシ Isodon trichocarpus KUDO の茎の成分研究
• Terpenoids(第6報) : ヒキオコシ Isodon japonicus HARA から Enmein および Enmein 3-acetate の分離について
• Lythraceous Alkaloids. XIV. Kinetic Equalization of Carbon-13 Nuclear Magnetic Resonance Chemical Shifts in N, O-Dimethyllythranidine, a Cyclophane Bearing Asymmetric Carbon Atoms
• Lythraceous Alkaloids. XIII. X-Ray Determination of the Molecular Structures of O-Methyllythranidine N, O, O-Triformate, 22-Bromolythranine N, O, O-Triacetate, and O-Methyldeacetyllythramine
• Lythraceous Alkaloids. XII. Circular Dichroism Studies on Lythranine-Type Alkaloids
• Lythraceous Alkaloids. X. Alkaloids of Lagerstroemia subcostata and L. favriei : A Contribution to the Chemotaxonomy
• Studies on the Alkaloids of the Root of Physalis alkekengi. (1). Isolation of 3α-Tigloyloxytropane
• Studies on the Constituents of the Seeds of Hernandia ovigera L. IV. Syntheses of β-Peltatin-A and-B Methyl Ethers from Desoxypodophyllotoxin
• Lythraceous Alkaloids. II. The Structure of O-Methyllythranidine
• Spectroscopic Identification of 3-Substituted 4-Methoxycarbonyl-1,3-thiazolidine(or-oxazolidine)-2-thiones and 2-Substituted Thio-4-methoxycarbonyl-Δ^2-1,3-thiazolines(or -oxazolines)
• Substituent Effect of the Benzene Ring on Thermal Rearrangement of the Substituted Benzyl Group from exo-S to N(3) in (rac)2-Substituted Benzylthio-4-methoxycarbonyl-Δ^2-1,3-thiazolines
• Syntheses of (rac)3-Substituted 4-Methoxycarbonyl-1,3-thiazolidine-2-thiones via Rearrangement of a Substituted Group from exo-S to N in (rac)2-Substituted Thio-4-methoxyarbonyl-Δ^2-1,3-thiazolines
• 56 シイタケ菌発育阻害因子,Trichopolynの構造研究
• Cytotoxic Activity of Marine Algae and a Cytotoxic Principle of the Brown Alga Sargassum tortile
• Cytotoxic Triterpenes from a Chinese Medicine, Goreishi
• Terpenoids. LIII. : Antitumor Activity of Trichorabdals and Related Compounds
• Terpenoids. LII. : The Structures of Trichorabdal F, Trichorabdal G Acetate, and Trichorabdal H. A Comment on the Structure of Shikodonin
• Terpenoids. LI. : Structures of Antitumor Diterpenoids, Trichorabdals A-E, Isolated from Rabdosia trichocarpa
• Terpenoids. L. Antitumor Activity of Diterpenoids from Rabdosia shikokiana var. occidentalis
• Terpenoids. XLVIII. New Diterpenoids from Rabdosia shikokiana var. occidentalis
• Hard Acid and Soft Nucleophile System. VII. A Convenient Reduction of Functionalized Polyarenes to Parent Polyarenes
• ANTITUMOR ACTIVITY OF DITERPENOIDS, TRICHORABDALS A, B, AND C, AND THE RELATED COMPOUNDS : SYNERGISM OF TWO ACTIVE SITES
• RADICAL CATION INDUCED REDUCTIVE DEHALOGENATION OF ORTHO- AND PARA-HALOPHENOLS AND THEIR DERIVATIVES
• Hard Acid and Soft Nucleophile System. VI. A Convenient Synthesis of Alkylthiopolycyclic Aromatics with a Metal Halide and Thiol System
• Studies on the Alkaloids of Thalictrum Thunbergii DC. XVIII. Total Synthesis of optically Active Natural O-Methylthalicberine
• Studies on the Acyl Glycosides from Leucoseptrum japonicum (MIQ.) KITAMURA et MURATA
• SELECTIVE DEMETHYLATION OF ALIPHATIC METHYL ETHER IN THE PRESENCE OF AROMATIC METHYL ETHER WITH THE ALUMINUM CHLORIDE-SODIUM IODIDE-ACETONITRILE SYSTEM
• Terpenoids. XLIX. Reactions of Shikoccin : Oxidation, Catalytic Reduction, and Conversion into the Abietane Skeleton
• THREE NEW 8,9-SECO-ENT-KAURANE DITERPENOIDS FROM RABDOSIA SHIKOKIANA (LABIATAE)
• SYNTHESIS, STRUCTURE, AND SELF-OXIDATION OF ALKYNYL(PHENYL)IODONIUM PERIODATES
• Hard Acid and Soft Nucleophile System. IV. Removal of Benzyl Protecting Group with Boron Trifluoride Etherate and Dimethyl Sulflide
• The Effect of the Alkaline Earth Salts on the NMR Spectrum of Phenols
• Terpenoids. XXXVII. Hypoiodite Reactions with 6-Hydroxy-17-norkaurane- and 7-Norgibberellane-derivatives
• 22 C_ジベレリンの合成研究
• 13 核間窒素原子を有する二環性アルカロイドの単純化不斉合成(口頭発表の部)
• A CONVENIENT METHOD FOR THE SYNTHESIS OF αβ-UNSATURATED CARBOXYLIC ACID AMIDES UTILIZING A NEW HETERO-BIFUNCTIONAL REAGENT, DMPATT
• Silicon-Assisted Ring Opening of Cyclopropyl Ketones with Boron Trifluoride-Acetic Acid Complex
• Stereoselective Syntheses of E- and Z-9,11-Dodecadien-1-yl Acetates : The Major Sex Pheromones of the Red Bollworm Moth
• Umpolung of Reactivity of Allylsilane, Allylgermane, and Allylstannane via Their Reaction with Thallium (III) Salt : A New Allylation Reaction for Aromatic Compounds
• Umpolung of Reactivity of Allylsilane, Allylgermane, and Allylstannane : Allylation of Aromatic Compounds with Allylmetal and Arylthallium Bis (trifluoroacetate)
• アリルケイ素化合物を用いる有機合成反応--特にアリルカチオン等価体としての有用性 (「有機ケイ素化合物の化学とその応用」特集号)
• Kaurene関連ジテルペンの反応および合成 (天然物化学′80A)
• Terpenoids. XLIII. Total Synthesis of rac-Kaur-16-ene-11α, 15α-diol
• Terpenoids. XLII. A Convenient Stereoselective Transformation of 16-Exocyclic Methylene Group into Carboxy Group in ent-Kaurene and Its 19-Oic Acid
• 28 硝酸タリウム(III)を用いるkaurene型ならびに関連ジテルペン類の酸化および転位反応
• Terpenoids. XXXIII. Chemical Conversion of Enmein into Enmelol
• Terpenoids. XXVI. Structures of Lasiokaurinol and Lasiokaurinin, Two Novel Diterpenoids of Isodon lasiocarpus (HAYATA) KUDO
• Terpenoids. XX. The Structure and Absolute Configuration of Lasiokaurin and Lasiodonin, New Diterpenoids from Isodon lasiocarpus (HAYATA) KUDO
• Iodine (III)-Mediated Intramolecular Cyclization of Hydroxy Allylsilanes : Synthesis of 5- or 6-Membered β-Methylene Cyclic Ethers
• Iodine (III)-Mediated Allylation of Aromatic Compounds and Alcohols Using Allylmetal (Group IVb) Compounds
• Thallium (III)-Mediated Allylation of Alcohols and Carboxylic Acids : Umpolung of Reactivity of Allylmetal (Group IVb) Compounds
• Facile 1,4-Silyl Rearrangement with Concomitant Loss of a Benzenesulfonyl Group : One-Pot Synthesis of Allyloxysilanes
• A New Synthesis of Olefins via the Elimination Reaction of β-Tributylstannyl Organosulfur Compounds
• A New Synthesis of Allyl Nitrates from Allylmetal (Group IVb) Compounds and Thallium (III) Nitrate
• A NEW METHOD FOR REGIOSELECTIVE SYNTHESIS OF α-SUBSTITUTED ALLYLSILANES AND ITS APPLICATION TO THE SYNTHESIS OF E- AND Z-TAGETONES
• New Allylation Reaction using Allylmetal (Group IVb) Compounds : Synthesis of N-Allylamides
• Reactions of Enmein-type Compounds with Lead Tetraacetate Iodine under Irradiation
• Diazidation of Allylsilanes with a Combination of Iodosylbenzene and Trimethylsilyl Azide, and Synthesis of Allyl Azides
• スペルミジンシデロホア,パラバクチンの全合成(発表論文抄録(1984年),福山大学開学10周年記念号)
• テルペノイド(第23報)カウレンのヒドラジン-ヒドラジン塩酸塩での還元
• Studies on the Constituents of the Seeds of Hernandia ovigera L. VII. : Syntheses of (±)-Hernolactone and (±)-Hernandin
• Studies on the Constituents of the Seeds of Hernandia ovigera L. IX. Identification of Two Dibenzylbutyrolactone-Type Lignans and an Attempt of Conversion into Phenyltetralin-Type Lignan
• Studies on the Constituents of the Seeds of Hernandia ovigera L. VIII. Syntheses of (±)-Desoxypodophyllotoxin and (±)-β-Peltatin-A Methyl Ether
• Studies on the Constituents of the Seeds of Hernandia ovigera L. VI. Isolation and Structural Determination of Three Lignans(Pharmacognosy,Chemical)
• Studies on the Constituents of the Seeds of Hernandia ovigera L. V. : Syntheses of Epipodophyllotoxin and Podophyllotoxin from Desoxypodophyllotoxin
• Studies on the Constituents of the Seeds of Hernandia ovigera L. III. Structures of Two New Lignans
• C-Glycosylflavones in Lespedeza cuneata
• Plant Constituents biologically Active to Insects. I. Feeding Stimulants for the Larvae of the Yellow Butterfly, Eurema hecabe mandarina. (1)
• 61 新しい不斉アルキル化デザインを基盤とする二環性アルカロイド合成(口頭発表の部)
• Burgenstock立体化学会議
• オクテット
• 有機合成における保護基 : その最近の進歩
• A Versatile Synthesis of (±)-Solenopsin A
• 「薬学生の一般教育をより意義あるものにするためには」のパネルを読んで
• メリットを生かして合理的な運用を(ポスターセッションを考える)
• 6 グラヤノトキシン類の合成研究
• エステルエノレートアルキル化反応におけるアリル位置換基の立体電子的効果
• β-スタンニル有機硫黄化合物のβ-脱離反応を活用するビニルスルホン類の脱スルホン化反応 (有機金属化合物とその応用)
• アリルケイ素化合物を用いる有機合成反応 : 特にアリルカチオン等価体としての有用性
• 生理活性物質に対する新しい合成戦略 (新しい有機合成の展望--第一線化学者の考え方・進め方)
• 高選択的不斉誘導法
• 若干の大環状アルカロイドの合成
• Total Synthesis of Optically Active Natural O-Methylthalicberine
• サツマイナモリ Ophiorrhiza japonica B_L. の成分研究

もっと見る 閉じる

スポンサーリンク