Synthetic Studies on Aphidicolane and Stemodane Diterpenes. II. Neighboring Hydroxyl Group Participation in Stereoselective Syntheses of Tricyclo[6.3.1.0^<1,6>]dodecanes Corresponding to the B/C/D-Ring Systems

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概要

• 論文の詳細を見る

• Tricyclo[6.3.1.0^<1.6>]dodecane derivatives (5 and 6) corresponding to the B/C/D-ring systems of aphidicolane and stemodane diterpenes were synthesized stereoselectively via a spirodienone-alcohol (4) as a common intermediate. Participation of the neighboring hydroxyl group in 4 is crucial for controlling the stereochemistry of the spirocenters.

• 社団法人日本薬学会の論文
• 1993-11-15

著者

• 山下 博

  阪大院薬

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 徹明

  Faculty of Pharmaceutical Sciences, Osaka University

• 村上 和夫

  Faculty of Pharmaceutical Sciences, Osaka University

• 奥田 修

  Faculty of Pharmaceutical Sciences, Osaka University

• 黒田 武志

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 村上 和夫

  阪大院薬

• 森江 俊哉

  Faculty Of Pharmaceutical Sciences Osaka University

• 前崎 直容

  Faculty of Pharmaceutical Sciences, Osaka University

• 山下 博

  Faculty of Pharmaceutical Sciences, Osaka University

• 黒田 武志

  Faculty Of Pharmaceutical Sciences Osaka University

• 山下 博

  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

• 前崎 直容

  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

• Tanaka T

  Osaka Univ. Osaka Jpn

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• Kuroda Takeshi

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Tanaka Tetsuaki

  Faculty Of Pharmaceutical Sciences Osaka University

• Imanishi Takeshi

  Graduate Shool Of Pharmaceutical Sciences Osaka University

• Okuda O

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 奥田 修

  Faculty Of Pharmaceutical Sciences Osaka University

• Kuroda T

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

• Murakami K

  Osaka Univ. Osaka Jpn

• Murakami K

  阪大院薬

関連論文

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• 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
• 102(P-59) (±)-Scopadulinの全合成(ポスター発表の部)
• 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
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• 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
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• 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
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• A Modified Procedure for the Synthesis of Spirodienones from Phenolic α-Diazoketones
• Nucleotide Sequences of Membrane-Bound Hydrogenase Gene in Alcaligenes hydrogenophilus
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• Neighboring Hydroxyl Group Participation in Metal-Ammonia Reduction of Spirocyclic Dienones
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• A New Synthesis of α-Chamigrene
• Regioselective Functionalization of the Methylene Group Adjacent to Cyclopropyl Sulfide via Mercury(II)-Mediated Regioselective Ring-Opening Reaction
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• 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
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• 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
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• 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
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• 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
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• 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
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• 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
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