Synthetic Study on Gymnomitrol and Related Compounds. I.Preparation and Cyclopropane Ring Opening of 1,2,6-Trimethyltetracyclo[5.3.1.0^<2,6>.0<8,11>]undecan-9-one

スポンサーリンク

概要

• 論文の詳細を見る

• 1,2,6-Trimethyltetracyclo[5.3.1.0^<2,6&tg;.0<8,11>]undecan-9-one (4) was prepared from 1,5-dimethylbicyclo[3.3.0]octan-3-one (6) in fourteen steps. Its cyclopropane ring opening reaction was examined under various conditions. In all runs, 11-substituted 1,2,6-trimethyltricyclo[5.3.1.0^<2,6>]undecan-9-ones 20 were obtained as major products along with 7-substituted 1,2,8-trimethyltricyclo[6.3.0.0<2,6>]undecan-4-ones 21 and two other products 22 and 23.

• 社団法人日本薬学会の論文
• 1993-01-15

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 徹明

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 今西 武

  大阪大学大学院薬学研究科

• 岩田 宙造

  阪大院薬

• 田中 徹明

  阪大院薬

• 田中 徹明

  Faculty Of Pharmaceutical Sciences Osaka University

• Tanaka T

  Kvushu Univ. Fukuoka Jpn

• 山下 正行

  Faculty of Pharmaceutical Sciences, Osaka University

• 広川 美視

  Faculty of Pharmaceutical Sciences, Osaka University

• 宮下 和之

  Faculty of Pharmaceutical Sciences, Osaka University

• Tanaka T

  Osaka Univ. Osaka Jpn

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• Tanaka Tetsuaki

  Faculty Of Pharmaceutical Sciences Osaka University

• Imanishi Takeshi

  Graduate Shool Of Pharmaceutical Sciences Osaka University

• 広川 美視

  Dainippon Pharmaceutical Co. Ltd.

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

• 宮下 和之

  大阪大学大学院薬学研究科

• 宮下 和之

  Faculty Of Pharmaceutical Sciences Osaka University

• 山下 正行

  Faculty Of Pharmaceutical Sciences Osaka University

• 広川 美視

  Faculty Of Pharmaceutical Sciences Osaka University

関連論文

• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. IV.A Stereoselective Formal Total Synthesis of (±)-Aphidicolin
• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. III.An Alternative Stereoselective Access to Aphidicolane-Type B/C/D-Ring System
• 61 アフィディコラン型およびステモダン型ジテルペンの合成研究(ポスター発表の部)
• スカベンジャー受容体ノックアウトマウスを用いたDNAの取り込み機構の解析
• Structure-Activity Relationship Study of TXA_2 Receptor Antagonists. 4-[2-(4-Substituted Phenylsulfonylamino)ethylthio]phenoxyacetic Acids and Related Compounds
• Synthesis and Evaluation of Novel Thiazolidine Derivatives as Thromboxane A_2 Receptor Antagonists
• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. II. Neighboring Hydroxyl Group Participation in Stereoselective Syntheses of Tricyclo[6.3.1.0^]dodecanes Corresponding to the B/C/D-Ring Systems
• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. I. Synthesis of (2'R^*, 4a'S^*, 8a'R^*)-2', 8a'-Dimethyl-4a', 5', 8', 8a'-tetrahydrospiro [2,5-cyclohexadiene-1,1'(2H)-naphthalene]-3'(4'H), 4,6' (7'H)-trione
• Synthetic Studies on Spiroketal Natural Products. V. Total Synthesis of (+)-Talaromycin A and (-)-talaromycin B
• Synthetic Studies on Spiroketal Natural Products. IV.A Stereoselective Synthesis of (3S, 5S, 6R, 9R, R_S)-3-Benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro[5.5]undecane, a Key Intermediate for Talaromycins
• Synthetic Studies on Spiroketal Natural Products. II. An Enantioselective Synthesis of (R)- and (S)-1,7-Dioxaspiro[5.5]undecane
• Synthetic Studies on Spiroketal Natural Products. I. : A Stereoselective Synthesis of (2R^*, 5R^*)- and (2R^*, 5S^*)-2-Methyl-1,6-dioxaspiro[4.5]decane
• Synthetic Studies on Aphidicolane and Stemodane Diterpenes. V. A Facile Formal Total Synthesis of (±)-Aphidicolin via a Lewis Acid-Mediated Stereoselective Spiroannelation
• Lewis Acid-Mediated Stereoselective Spiroannelation : A Facile Access to Aphidicolane and Stemodane B/C/D Ring Systems
• Synthetic Studies on Aromadendrane-Type Compounds. II.Stereoselective Synthesis of (+)-1,2-Didehydroaromadendrane
• Synthetic Studies on Aromadendrane-Type Compounds. I. Stereoselective Construction of Aromadendrane- and Alloaromadendrane-Type Skeletons
• Construction of Asymmetric Quaternary Carbon Center Containing Heteroatom via Regioselective Cleavage of Cyclopropane Ring Mediated by Mercury(II) Salt
• Synthetic Study on Gymnomitrol. II. A Synthesis of (±)-Isogymnomitrol
• Synthetic Study on Gymnomitrol and Related Compounds. I.Preparation and Cyclopropane Ring Opening of 1,2,6-Trimethyltetracyclo[5.3.1.0^.0]undecan-9-one
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. VI. An Improved Formal Synthesis of (±)-Descarboxyquadrone via Highly Regioselective Cyclopropane Ring Opening of Tricyclo[3.3.0.0^]octan-3-one
• 1,6-Dihydro-3 (2H)-pyridinones. II. Synthesis of 2-Azabicyclo [2. 2. 2] octanes by the Reaction of N-Substituted 1,6-Dihydro-3 (2H)-pyridinones with 1,3-Dicarbonyl Compounds
• 1,6-Dihydro-3 (2H)-pyridinones. I. Facile Synthesis of N-Substituted 1,6-Dihydro-3 (2H)-pyridinones
• 2-Oxo-1,2,3-oxathiazolidines. Its Application to Separation of Diastereoisomers of β-Amino-alcohols, 6-(4-Methoxy-2-piperidyl)-1,4-dioxaspiro [4,5] decan-6-ol and 2-Hydroxy-2-(2-piperidyl) cyclohexanone
• Synthetic Studies on Securitinine and Related Compounds. II. A Synthesis of 10a-Episecuritinine
• Synthetic Studies on Securitinine and Related Compounds. I. Stereochemistries of the Catalytic Hydrogenation Products of 6-(4-Methoxy-2-pyridyl)-1,4-dioxaspiro [4,5] decan-6-ol
• Transformation of (±)-Ophiocarpine and (±)-13-Epiophiocarpine to (±)-α- and (±)-β-Hydrastine with Complete Retention of Configuration
• Studies on Ergot Alkaloids and Related Compounds. XIII. syntheses and Stereochemistries of 4-Methyl-1,2,3,-4,4a, 5,6,10b-octahydrobenzo[f]quinoline-2-carboxylic Acids
• Platelet Anti-aggregant Activity of 2,2-Dimethylthiazolidine Hydrochloride and 2-(4-Hydroxy-3-methoxyphenyl)thiazolidine
• 3-Hydroxypyrroles. III. Synthesis and Tautomerism of N-Alkyl-3-hydroxypyrroles
• Octahydro-7 (1H)-quinolones. VII. A Stereoselective Synthesis of cis, trans-Decahydro-3H, 8H-benzo [i, j] quinolizine-3,8-dione
• 3-Hydroxypyrroles. II. The Reaction of 4,5-Unsubstituted Alkyl 3-Hydroxypyrrole-2-carboxylates with Some Electrophiles
• 10 リコポジウムアルカロイドの合成研究 : (±)-Anhydrolycodoline及び(±)-Lycopodineの全合成
• A New Synthesis of (±)-Agarospirol and (±)-Hinesol
• Synthetic Studies on Quadrone. I. An Approach to the Synthesis of (±)-Quadrone(Organic,Chemical)
• A FORMAL TOTAL SYNTHESIS OF (±)-QUADRONE
• Synthetic Studies on Acorane-Alaskane Sesquiterpenes. I. Total Synthesis of (±)-β-Acorenol
• Excellent Chiral Induction by Diene Iron-Tricarbonyl Moiety. I : Diastereoselective [4+2] Type Cycloaddition of 1-Azatriene Iron-Tricarbonyl Complex
• A Modified Procedure for the Synthesis of Spirodienones from Phenolic α-Diazoketones
• Nucleotide Sequences of Membrane-Bound Hydrogenase Gene in Alcaligenes hydrogenophilus
• Biogenetic-Type Transformation of α-[α-(Hydroxymethyl)-3,4-dimethoxystyryl]-3,4-methylenedioxycinnamic Acid γ-Lactone into Diphyllin
• 3-Hydroxypyrroles. I. A General Synthetic Route to 4,5-Unsubstituted Alkyl 3-Hydroxypyrrole-2-carboxylates
• Studies on the Syntheses of Spiro-dienone Compounds. VII. Novel Synthesis of the Spiro [4.5] decane Carbon Framework
• Synthetic Studies on Quadrone. II. Synthesis of Methyl (1R^*,3aR^*,6aR^*)-2,2-Dimethyl-2,3,3a,4,6,6a-hexahydro-1-(2-hydroxyethyl)-4-methylene-5-oxo-3a(1H)-pentaleneacetate, a Key Intermediate for the Synthesis of (±)-Quadrone(Organic,Chemical)
• Synthetic Studies on Spirovetivane Phytoalexins. III. : A Total Synthesis of (±)-Lubiminol
• Synthetic Studies on Spirovetivane Phytoalexins. II. : Stereoselective Synthesis of (2RS, 5RS, 6SR, 8RS, 10SR)-6-Hydroxymethyl-8-methoxymethoxy-10-methyl-2-pivaloyloxyspiro[4.5]decane
• Neighboring Hydroxyl Group Participation in Metal-Ammonia Reduction of Spirocyclic Dienones
• Synthetic Studies on Acorane-Alaskane Sesquiterpenes. II. : Total Synthesis of (±)-Acorenone
• Total Synthesis of (±)-α-Chamigrene and Brominated Chamigrene
• A New Synthesis of α-Chamigrene
• Regioselective Functionalization of the Methylene Group Adjacent to Cyclopropyl Sulfide via Mercury(II)-Mediated Regioselective Ring-Opening Reaction
• Asymmetric Cyclopropanation by Reaction of a γ-Chloromethylated Chiral Vinylic Sulfoxide with Allylmagnesium Bromide
• Synthetic Studies on Spirovetivane Phytoalexins. V. : A Stereoselective Total Synthesis of (±)-Oxylubimin
• Synthetic Studies on Spirovetivane Phytoalexins. IV. : A Stereoselective Synthesis of (±)-3-Hydroxysolavetivone
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-r-ones as Synthetic Intermediates. V. : An Improved Synthesis of (±)-Pentalenene
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. IV. : A Further Examination of Cyclopropane Ring Opening in the Tricyclo[3.3.0.0^]octan-3-one System
• Synthetic Studies on Spiroketal Natural Producys. III. : Enantioselective Synthesis of 1,6-Dioxaspiro[4.5]decane Compounds
• Studies on Ergot Alkaloids and Its Related Compounds. X. Condensation of Cyclic Ketones and 3-Methylaminopropionates
• 1,6-Dihydro-3 (2H)-pyridinones. V. Total Synthesis of (±)-Eburnamonine
• 1,6-Dihydro-3 (2H)-pyridinones. IV. Synthesis of (±)-Tabersonine and (±)-Cleavamine via a Common Intermediate, Ethyl 3-Ethyl-3-hydroxy-1,2,3,6-tetrahydropyridine-1-carboxylate
• 1,6-DIHYDRO-3 (2H)-PYRIDINONES AS SYNTHETIC INTERMEDIATES. TOTAL SYNTHESIS OF (±)-EBURNAMONINE
• 1,6-Dihydro-3 (2H)-pyridinones as Synthetic Intermediates. A Convenient Total Synthesis of (±)-Cleavamine
• Total Synthesis of (±)-Solavetivone and Aglycone A_3. Regio-and Stereo-Selective Birch Reduction of 6,10-Dimethyl-2-hydroxy-spiro[4.5]deca-6,9-dien-8-one(Organic,Chemical)
• An Approach to the Stereoselective Synthesis of Nidifocene. II.Total Synthesis of (±)-Dehalogenonidefocene
• 7,7-Dimethyltricyclo[3.3.0.0.^]octan-3-ones as Synthetic Intermediates. I. : Preparation and Cyclopropane Ring Opening of 7,7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.0^]octan-3-one
• Stereochemistry of the Intramolecular Cyclization Products of Methyl 2-Bromo-5-(4-hydroxyphenyl) hexanoate : Synthesis of trans- and cis-1,4-Dimethyltetralin
• Photochemical Oxidation. II. Biogenetic-Type Conversion of Ligularol and Furanoeremophilane into 6β-Hydroxyeremophilenolide and Eremophilenolide
• 1,6-Dihydro-3 (2H)-pyridinones. VIII. Total Synthesis of (±)-Corynantheidol and Formal Synthesis of (±)-Quinine
• 1,6-Dihydro-3 (2H)-pyridinones. VI. Introduction of an Amidocarbonylmethyl Chain at C-4 of the 1,6-Dihydro-3 (2H)-pyridinone Nucleus via Photochemical [2+2] Cycloaddition Reaction
• 1,6-DIHYDRO-3 (2H)-PYRIDINONES AS SYNTHETIC INTERMEDIATES. STEREOSELECTIVE SYNTHESIS OF (±)-CORYNANTHEIDOL AND (±)-QUININE
• An Approach to the Stereoselective Synthesis of Nidifocene. III.Total Syntheses of the Stereoisomers of (±)-Nidifocene from(±)-Dehalogenonidifocene
• An Approach to the Stereoselective Synthesis of Nidifocene : Regio- and Stereoselective Synthesis of vic-trans-Bromochlorocyclohexane Ring System
• Synthesis of Four Possible Isomers of 9-(Bromomethylene)-1,2,5-trimethylspiro[5.5]undeca-1,7-dien-3-one : Structure Elucidation of a Brominated Rearranged Chamigrane-Type Sesquiterpene
• Octahydro-7 (1H)-quinolones. IV. Construction of Decahydro-3H, 10H-benzo [i, j] quinolizine-3,10-dione Systems from cis-and trans-Octahydro-7 (1H)-quinolone
• Octahydro-7 (1H)-quinolones. III. cis-trans Isomerization of Octahydro-7 (1H)-quinolone Analogues
• Octahydro-7 (1H)-quinolones. II. A Stereoselective Synthesis of cis-Octahydro-7 (1H)-quinolone
• Octahydro-7 (1H)-quinolones. I. Stereochemistries of Catalytic Hydrogenation of 7-Hydroxyquinoline
• Studies on the Syntheses of Spiro-dienone Compounds. V. An Improved Synthetic Method of Spiro-dienone Compounds. Syntheses of dl-Mecambrine, dl-Amurine and dl-Domesticine
• NOVEL AND CHIRAL HANTZSCH-TYPE 1,4-DIHYDROPYRIDINES HAVING A p-TOLYLSULFINYL GROUP. SYNTHESIS AND BIOLOGICAL ACTIVITIES AS CALCIUM CHANNEL ANTAGONISTS
• 1,6-Dihydro-3 (2H)-pyridinones. X. 2-Azabicyclo [2.2.2] octane Ring Formation via Intramolecular Michael Reaction : Total Synthesis of (±)-Ibogamine and (±)-Epiibogamine
• 1,6-Dihydro-3 (2H)-pyridinones. VII. Stereoselective Total Synthesis of a Monoterpene Alkaloid, (±)-Tecomanine
• 1,6-Dihydro-3 (2H)-pyridinones. III. A Formal Synthesis of (±)-Catharanthine
• 57 1,6-ジヒドロ-3(2H)-ピリジノンを合成素子とするアルカロイド合成 : (±)-Ibogamine,(±)-Epiibogamine,及び(±)-Tecomanineの全合成
• 44 1,6-ジヒドロ-3(2H)-ピリジノンを合成素子とするインドールアルカロイド類の合成研究
• 1,6-Dihydro-3 (2H)-pyridinones. IX. A Regioselective Synthesis of Ethyl 3-Methoxycarbonylmethyl-4-oxopiperidine-1-carboxylate from Ethyl 3-Hydroxy-1,2,3,6-tetrahydropyridine-1-carboxylate
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. III. : Total Synthesis of (±)-Descarboxyquadrone
• 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. II. : A Total Synthesis of (±)-Pentalenene, an Angular Triquinane Sesquiterpene
• Synthesis of (±)-Hydroxysugiresinol (Sequirin B) Trimethyl Ether
• Photochemical Enolization of ortho-Alkylbenzaldehydes
• Synthetic Studies on the Lycopodium Alkaloids. III. Synthesis of a Key Intermediate, Ethyl Octahydro-4aβ-hydroxy-7β-methyl-10-oxo-1H-5,8α-propanoquinoline-1-carbamate, for the Lycopodium Alkaloids
• Synthetic Studies on the Lycopodium Alkaloids. II. A Synthesis of a Key Intermediate, 2,3,5,6,7,8-Hexahydro-7β-methyl-3-oxo-1H-5,8a-propenoquinoline, for the Lycopodium Alkaloids
• Preparations and Stereochemistries of Ethyl 3α- and 3β-Methyl-9-oxobicyclo (3,3,1) nonane-1-carboxylates and Related Compounds
• Studies on Azasteroids and Related Compounds. III. On the Cyclodehydration of Cyclic Ketone and β-Aminoester
• 45 Tricyclo[3.3.0.0^]octan-3-one化合物を鍵中間体とするポリキナン型セスキテルペン類の合成研究 : (±)-Pentalenene及び(±)-Quadroneの全合成
• TOTAL SYNTHESIS OF (±)-PENTALENENE
• ジヒドロピリジノンを共通出発原料としたアルカロイド類の合成
• Studies on the Syntheses of Spiro-dienone Compounds. VI. A New Synthesis of dl-Pronuciferine.
• Studies on the Syntheses of Spiro-dienone Compounds. IV. Photolysis of Sodium Salts of p-[2-(2-Halogenomethyl-1,3-dioxolan-2-yl)-ethyl] phenol in N, N-Dimethylformamide
• Studies on the Syntheses of Spiro-dienone Compounds. III. Photolysis of 2-Halogeno-N-ethyl-4'-hydroxybenzanilide in Aqueous Sodium Hydroxide
• Studies on Ergot Alkaloids and Related Compounds. XI. Synthesis of trans-and cis-4-Mehyl-1,2,3,4,4a, 5,6,10b-octahydrobenzo [f] quinoline
• Studies on Ergot Alkaloids and Related Compounds. IV. Preparation and Lithium Aluminum Hydride Reduction of Some Vinylogous Lactams.

もっと見る 閉じる

スポンサーリンク