Syntheses of several cyclopentano-monoterpene lactones using 1,3-dioxin vinylogous ester

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概要

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• Formal syntheses of (±)-boschnialactone (5) and three cyclopentano-monoterpene lactones [i.e., (±)-(iridomyrmecin (6), (±)-isoiridomyrmecin (7), and (±)-allodolicholactone (8)] have been accomplished in the form of the syntheses of 2-(methoxymethyl)-3-methyl-2-cyclopenten-1-one (11) and (±)-(4aα,7α,7aα)-hexahydro-7-methylcyclopenta[c]pyran-3(1H)-one (19), respectively, starting from 6,7-dihyd;ocyclopenta-1,3-dioxin-5(4H)-one (2). A synthesis of (±)-isodehydroiridomyrmecin (9) has also been achieved through a route including direct substitution of the hydroxy group of 2-(tert-butyldimethylsilyloxymethyl)-3- methyl-2-cyclopenten-1-ol (22) with 1-(tert-butyldimethylsilyloxy)-1-methoxyethene (23) as a key step.

• 公益社団法人日本薬学会の論文
• 1995-01-15

著者

• 藤井 澄三

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  金沢大学薬学部

• 大場 正志

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 大場 正志

  Kanazawa Univ. Ishikawa Jpn

• 羽石 剛

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Ohba M

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 羽石 剛

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

関連論文

• Lactams. XIII. Alkylation of Lactim Ethers : A Novel Synthetic Route to N-(2-Arylethyl) lactams from N-Unsubstituted Lactams
• Purines. LXX. An Extension of the "Phenacylamine Route" to the Syntheses of the 7-N-Oxides of 6-Mercaptopurine and 6-Methylthiopurine, and Antileukemic Activity of Some Purine N-Oxides
• Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
• Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
• Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
• Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
• Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
• Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
• Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
• Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
• Lactams. VII. Stereochemical Characterization and Cis-Trans Isomerization of 5-Ethyl-2-oxo-4-piperidineacetic Acid and Related Compounds
• Lactams. XVII. Synthesis and Stereochemical Characterization of Diethyl cis-and trans-5-Ethyl-2-oxo-4-piperidinemalonate
• Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
• Purines. XLI. : An Alternative Synthesis and the Chemical Behavior of 7,9-Dialkyladeninium Salts
• Purines. XXXVIII. A General Synthesis of 7,9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N^6-Alkoxy Group as a Control Synthon
• Purines. XXX. : Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis
• Purines. XXVIII. Preparation of Some 3,7-Dialkyladenines from 3-Alkyladenines by Alkylation : A Subordinate Formation of 3,9-Dialkyladenines
• Purines. XXI. Synthesis of Adenine 1-Oxides Carrying an Allylic Side Chain at the 9-Position
• Lactams. XX. Decarboxylation of Unsaturated Acids incorporated into Six-Membered Lactam Systems
• Lactams. VIII. The Alkaline Ferricyanide Oxidation of 3-Substituted 1-(3,4-Dimethoxyphenethyl) pyridinium Salts : Effects of Hydrocarbon Substituents on Orientation of the Oxidation
• Lactams. VI. Synthesis and Nuclear Magnetic Resonance Study of 1-Aralkyl-3-methyl- and -5-methyl-2(1H)-pyridones
• ゼアチンおよび N^6- イソペンテニルアデニンの 1'- メチル誘導体とそれらのリボヌクレオシド体のレタス種子発芽におけるサイトカイニン活性について(A. 理学)
• Purines. LXII. Both Enantiomers of N^6-(1,3-Dimetyl-2-butenyl)adenine and Their 9-β-D-Ribofuranosides : Synthesis and Cytokinin Activity
• Purines. LV. Syntheses and cytokinin activities of some adenine and adenosine derivatives related to 1'-methylzeatin
• Pourines. XLV. : Syntheses and Cytokinin Activities of the Cis Isomers of (1'R)-1'-Methylzeatin and Its 9-β-D-Ribofuranoside
• Purines. XXXV. : Synthesis and Cytokinin Activity of Racemic 1'-Methylzeatin
• Purines. XXXIII. Syntheses and Cytokinin Activities of Both Enantiomers of 1'-Methylzeatin and Their 9-β-D-Ribofuranosides
• フリニルアミノ酸,フリニルヘフタイトおよび関連化合物のサイトカイニン活性について(A. 理学)
• Purines. XIX. The Direct N^6-Alkylation of 1-Alkoxy-9-alkyladenines : An Alternative Synthesis of N^6,9-Dialkyladenines
• Quinolizidines. VII. Structure of O-Methylpsychotrine : The Endocyclic versus the Exocyclic Double Bond Structure in the Dihydroisoquinoline Moiety
• Purines. LXV. Preparatory study for the syntheses of the marine sponge purines agelasimines-A and -B: Synthesis and acetylation of their N(7)-benzyl analogues
• Purines. LXIV. Syntheses of 9-Methyl-2-azaadenine 1-Oxide, Its O-Methyl Derivative, and 1-Substituted 5-Azidoimidazole-4-carboxamides
• Purines. LXIII. Syntheses of Azepinomycin, an Antitumor Antibiotic from Streptomyces Species, and Its 3-β-D-Ribofuranodise and Their 8-Imino Analogues
• Purines. LXI. An Attempted Synthesis of 2'-Deoxy-7-methyladenosine : Glycosidic Hydrolyses of the N^6-Methoxy Derivative and 2'-Deoxy N^x-methyladenosines
• Purines. LIX. An Alternative Synthesis of 7-Alkyl-1-methyladenines by Regioselective Alkylation, Fission, and Reclosure of the Adenine Ring
• Purines. LVIII. A Synthesis of 7-Alkyl-1-methyladenines from Adenosine by Regioselective Alkylation : Uilization of a 1-Methoxy Group as a Control Synthon
• Purines. LVII. Regioselective Alkylation of N^6,9-Disubstituted 8-Oxoadenines : Syntheses of the Sea Anemone Purine Caissarone and Some Positional Isomers and Analogues
• Purines. LIV. Intramolecular Cyclization of 9-Ethyl-1-(2-hydroxyethyl)adenine Caused by Nucleophiles : Formation of N^6,1-Ethanoadenine Derivatives
• Purines. LIII. Deamination of 1-(ω-Hydroxyalkyl)adenine Derivatives by Nucleophiles
• Purines. XLIX. Synthesis and Proton Nuclear Magnetic Resonance Study of 3,7-Dialkylxanthines and 1,3,7-Trialkylxanthines
• Purines. XLVIII. Syntheses and Proton Nuclear Magnetic Resonance Study of 2-Deuterioadenines Substituted or Unsubstituted at the 9-Position and of Their N-Oxygenated Derivatives
• Purines. XLVI. Preparation of 1-Ethyladenine from Adenosine
• Quinolizidines. XX. Racetnic and Chiral Syntheses of the Alangium Alkaloids 9-Demethylprotoemetinol and 10-Demethylprotoemetinol(Organic,Chemical)
• Lactams. XXVI. Regioselectivity in the mercuric acetate- edetic acid oxidation of the ethyl 1-(2-aryl-2-hydroxyethyl)-3- ethyl-4-piperidineacetate system: Enhancement by a benzyloxy group in the aryl moiety and by the 3,4-cis configuration
• Quinolizidines. XXV. : An Extension of the "Lactim Ether Route" to the Racemic Syntheses of Several Indolo[2,3-α]quinolizidine Alkaloids
• Quinolizidines. XVIII. Synthesis of (-)- and (+)-ankorines through a lactim ether route
• Quinolizidines. XIII. Syntheses of (±)-and (-)-Alangimarckines
• Lactams. XXIII. Thermal cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system: Effect of an N-substituent
• Preparation of Tyrosol and 4-Methoxyphenethyl Alcohol.
• Synthesis of 5-(Alkylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamides : Key Intermediates for the Synthesis of 3-Alkyl-9-β-D-ribofuranosylpurine Derivatives
• Purines. XXXII. : Synthesis and Ring Fission of 3,9-Dialkyladenines
• Purines. XXV. Fission and Reclosure of the Adenine Ring by the Use of Modified Benzyloxy Groups at the 1-Position
• Purines. XX. Synthesis of 1-Substituted 5-Aminoimidazole-4-carboxamidines and Related Compounds
• Purines. XIV. Selective Removal of N-Terminal Amino Acids from Peptides by the Use of Purin-6-yl Group at the N-Terminus
• Quinolizidines. XXXIII. A chiral synthesis of (-)-ophiorrhizine, a pentacyclic quaternary indole alkaloid from ophiorrhiza major RIDL
• Syntheses of several cyclopentano-monoterpene lactones using 1,3-dioxin vinylogous ester
• Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines
• [4,5-Dimethoxy-α-(3,4-dimethoxyphenyl)-o-tolyl]acetonitrile : A By-Product from the Reaction of 3,4-Dimethoxybenzyl Chloride with Sodium Cyanide
• Lactams. XXII. Preparation of the Enantiomers of 6-Ethoxy-3-ethyl-2,3,4,5-tetrahydro-4-pyridineacetic Acid Ethyl Ester
• Purines. XLVII. Dimroth Rearrangement versus Hydrolytic Deamination of 1-Ethyladenine
• Quinolizidines. XXX. A ready access to the dibenzo[a,f]quinolizidine ring system from 1,2,3,4-tetrahydroquinoline
• Syntheses of cis-Zeatin and Its 9-(2-Deoxy-β-D-ribofuranosyl) Derivative : A Novel Synthetic Route to the Side Chain at C(6), and Cytokinin Activity
• Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana
• Quinolizidines. XXVII. Racemic and chiral syntheses of the Neisosperma and Ochrosia alkaloid ochropposinine
• Quinolizidines. XXIV. : Syntheses of Ankorine Congeners in Different Oxidation States
• Quinolizidines. XIX. Synthesis of (-)-9-demethyltubulosine
• Lactams. V. Syntheses of 1-(2-Arylethyl)-3-alkyl-2- and -6-piperidones : A Comparative Study of the Mercuric Acetate-EDTA and the Ferricyanide Oxidation Methods
• Purines. XXXVII. : Synthesis and Reduction of 3,9-Diallkyladenine Salts Deuterated at the 2-Position : Their Use in the Proton Nuclear Magnetic Resonance Study of Isotopically Unmodified Species
• Purines.XXXIX. : The Crystal Structure of 9-Benzyl-N^6-methoxyadenine
• Purines. XXXI. : An X-Ray Crystallographic Structure Analysis of 3-Methyladenosine p-Toluenesulfonate
• An Improved Procedure for the Synthesis of 1-Alkyladenines : Removal of the Ribofuranosyl Group from 1-Benzyl-, 1-(3-Methyl-2-butenyl)-, and 1-Allyladenosine Hydrobromide in Acetic Acid
• Purines. XV. Conversion of N, 9-Dimethyladenine into the 1,9-Dimethyl Isomer : A Reverse Operation of the Dimroth Rearrangement
• Quinolizidines. XIV. A racemic synthesis of 9-demethyltubulosine, an alkaloid isolated from Alangium vitiense
• Purines. XLIV. : A Kinetic Study of the Dimroth Rearrangement of the Marine Sponge Purine 1,9-Dimethyl-8-oxoadenine and Related Compounds
• Purines. XLIII. : A Total Synthesis of the Marine Sponge Base 6-Imino-1,9-dimethyl-8-oxopurine
• Lactams. XV. Chemistry of Unsaturated δ-Valerolactams
• Lactams. XVIII. Oxidation of 1-Substituted 3-tert-Butyl-piperidine with Mercuric Acetate-EDTA
• Lactams. XIX. The Alkaline Ferricyanide Oxidation of 1,3-Disubstituted Pyridinium Salts : Effects of Branched Alkyl Groups at the 3-Position
• Synthesis of 3-tert-Butylpyridine
• Purines. XLII. : Synthesis and Glycosidic Hydrolysis of 7-Alkyladenosines Leading to an Alternative Synthesis of 7-Alkyladenines
• Purines. XL. : Preparation of 9-(ω-Carboxyalkyl)-3-methyladenines
• The Preparation of 3,4-Dimethoxy-and 3,4-Methylenedioxy-Phenethyl Alcohol
• Purines. XXXVI. : Fission and Reclosure of the Adenine Ring in 3,9-Disubstituted Adenines : Effects of Substituents
• Purines. XXXIV. : 3-Methyladenosine and 3-Methyl-2'-deoxyadenosine : Their Synthesis, Glycosidic Hydrolysis, and Ring Fission
• A General and Convenient Synthesis of 7-Alkyladenines from Adenine by Regioselective Alkylation Utilizing Blocking/Deblocking at the 3-Position
• Purines. XXVII. : Hydrolytic Deamination versus Dimroth Rearrangement in the 9-Substituted Adenine Ring : Effect of an ω-Hydroxyalkyl Group at the 1-Position
• Purines. XXVI. The Dimroth Rearrangement of 9-Substituted 1-Methyladenines : Accelerating Effect of a β-D-Ribofuranosyl Group at the 9-Position
• Purines. XXIV. Methylation of N^6-Alkoxyadenines and N^6-Methyladenine
• Purines. XIII. Ring Opening of 3-Alkyladenines with Carbobenzoxy Chloride : Transformation into 8-Hydroxylated Adenines
• Purines. X. A Convenient Method for Synthesis of 2', 3'-O-Isopropylidene-adenosine 1-Oxide
• Debenzylation of N-Benzyl-acylamides.
• Purines. XVIII. Kinetic Studies of the Dimroth Rearrangement of 1-Alkoxy-9-methyladenines and 1-Benzyloxyadenosine : Effect of 1-Benzyloxy and 9-β-D-Ribofuranosyl Groups on the Rates of the Ring-opening and the Reclosure
• Purines. XVI. One-Step Alkylation of Adenine 1-Oxide Leading to 1-Alkoxy-9-alkyladenine Hydriodide
• Quinolizidines. III. An Improved Synthetic Route to Stereoisomers of dl-2,3-cis-Emetine
• Quinolizidines. II. A Stereoselective Synthesis of Emetine
• Preparation of Some Ring-Oxygenated Phenacyl Bromides
• Lactams. XIV. cis-trans Isomerization in the 5-Ethyl-2-oxo-4-piperidineacetic Acid System under Fischer-Speier Esterification Conditions
• Lactams. XII. Improvements in the Synthesis of Ethyl trans-5-Ethyl-2-oxo-4-piperidineacetate
• Lactams. XI. Construction of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Carbonyl and Related Groups at the 3-Position
• Lactams. IX. Generation of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Hydrocarbon Substituents at the 3-Position

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