Synthetic Studies on Spirovetivane Phytoalexins. IV. : A Stereoselective Synthesis of (±)-3-Hydroxysolavetivone

スポンサーリンク

概要

• 論文の詳細を見る

• Oxidation of the silyl enol ether of (2RS, 5RS, 10RS)-6,10-dimethyl-2-pivaloyloxyspiro[4.5]dec-6-en-8-one (5) with triphenyl phosphite ozonide (TPPO) gave stereoselectively the C_9-hydroxylated derivative (6a), which was transformed into a spirovetivane phytoalexin, (±)-3-hydroxysolavetivone (1), by a several-step sequence.

• 公益社団法人日本薬学会の論文
• 1989-10-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 竹本 佳司

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  阪大院薬

• 中村 文胤

  日本新薬(株)知的財産部調査課

• Takemoto Yoshiji

  Faculty Of Pharmaceutical Sciences Osaka University

• Takemoto Y

  Graduate School Of Pharmaceutical Sciences Kyoto University

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• 中村 文胤

  Faculty of Pharmaceutical Sciences, Osaka University

• 中村 文胤

  田辺製薬 研究企画部

• 中村 文胤

  Faculty Of Pharmaceutical Sciences Osaka University

• 中村 文胤

  日本新薬(株)創薬研究所

• Imamura T

  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)
• 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
• Antiproliferative Activity of Rhinacanthus nasutus (L.) KURZ Extracts and the Active Moiety, Rhinacanthin C(Pharmacology)
• Efficient Chiral Induction by Diene Iron-Tricabonyl Moiety. IV. : Asymmetric Total Synthesis of a Piperidine Alkaloid, SS20846A
• Excellent Chiral Introduction by Diene Iron-Tricarbonyl Moiety. III : Asymmetric Synthesis of Hydroxyethylidene Dipeptide Isostere Using a Diastereoselective 1,2-Nucleophilic Addition of Organocerium Reagents into a 1-Azatriene Fe(CO)_3 Complex
• Excellent Chiral Introduction by Diene Iron-Tricarbonyl Moiety. II : A Formal Synthesis of (+)- and (-)-Frontalin Using a Diastereoselective 1,2-Nucleophilic Addition of Organometallics into a (Z)-Dienone Fe(CO)_3 Complex
• Transformation of (±)-Ophiocarpine and (±)-13-Epiophiocarpine to (±)-α- and (±)-β-Hydrastine with Complete Retention of Configuration
• Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural(2S, 3S)-Tartaric Acid
• 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
• A Highly Stereoselective Synthesis of (3S, 4S)-Statine and (3S, 4S)-Cyclohexylstatine
• Platelet Anti-aggregant Activity of 2,2-Dimethylthiazolidine Hydrochloride and 2-(4-Hydroxy-3-methoxyphenyl)thiazolidine
• Octahydro-7 (1H)-quinolones. VII. A Stereoselective Synthesis of cis, trans-Decahydro-3H, 8H-benzo [i, j] quinolizine-3,8-dione
• 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
• P-53 ジエン鉄カルボニル錯体を不斉発現素子とし用いた不斉合成反応の開発および生理活性物質の不斉合成(ポスター発表の部)
• 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
• 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
• 16 Spirovetivane型Phytoalexin類の合成研究 : (±)-Lubiminolおよび(±)-oxylubiminの立体選択的全合成
• 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.

もっと見る 閉じる

スポンサーリンク