Biogenetically Patterned Transformation of Eudesmanolide to Eremophilanolide. III. Acid Treatment of 4α, 5α-Epoxy-eudesman-8β, 12-olide
スポンサーリンク
概要
- 論文の詳細を見る
As a continuative study to clarify the structure requirement for the ready conversion of 5α, 6α-epoxy-eudesman-8β, 12-olide (1) to eremophilane-type compounds via the biogenetic-type 1,2-shift of 10-Me, acid treatment under a variety of acid conditions of 4α, 5α-epoxy-eudesman-8β, 12-olide (2) has been examined. It has been found that acid treatment of 2 with HCOOH-acetone, BF_3-etheratebenzene, CF_3COOH-CHCl_3,or p・TsOH・H_2O-EtOH furnish no eremophilane-type compound, but yield four products such as AT-1 (10), AT-2 (11), AT-3 (12), and AT-4 (13) with different compositions depending upon the reaction conditions. The reaction pathways are also discussed.
- 公益社団法人日本薬学会の論文
- 1975-11-25
著者
-
吉岡 一郎
Faculty Of Pharmaceutical Sciences Osaka University
-
北川 勲
Faculty of Pharmaceutical Sciences, Osaka University
-
渋谷 博孝
Faculty of Pharmaceutical Sciences, Osaka University
-
北川 勲
Faculty Of Pharmaceutical Sciences Osaka University
-
武野 秀一
Faculty of Pharmaceutical Sciences, Osaka University
-
武野 秀一
Faculty Of Pharmaceutical Sciences Osaka University
関連論文
- Structures of Echinoside A and B, Two Antifungal Oligoglycosides from the Sea Cucumber Actinopyga echinites (JAEGER)
- Marine Natural Products. XXIV. : The Absolute Stereostructure of Misakinolide A, a Potent Cytotoxic Dimeric Macrolide from an Okinawan Marine Sponge Theonella sp.
- Marine Natural Products. XXIII. : Three New Cytotoxic Dimeric Macrolides, Swinholides B and C and Isoswinholide A, Congeners of Swinholide A, from the Okinawan Marine Sponge Theonella swinhoei
- Marine Natural Products. XXII. : The Absolute Stereostructure of Swinholide A, a Potent Cytotoxic Dimeric Macrolide from the Okinawan Marine Sponge Theonella swinhoei
- STRUCTURE OF THEONELLAPEPTOLIDE ID, A NEW BIOACTIVE PEPTOLIDE FROM AN OKIKAWAN MARINE SPONGE, THEONELLA SP. (THEONELLIAE)
- The Revised Stereostructure of Patrinoside X-Ray Crystallographic Analysis
- Chemical Transformation of Terpenoids. X. Ionophoretic Activities of Macrocyclic Lactone Epoxides Synthesized from Geraniol
- Chemical Transformation of Terpenoids. IX. Ionophoretic Activities of Macrocyclic Lactone Epoxides Synthesized from E, E-Farnesol
- Syntheses of a Glycerophospholipid, C16-Platelet Activating Factor and a Palmitoyl Analogue of M-5,an Anti-inflammatory Glyceroglycolipid
- Syntheses of Two Pairs of Enantiomeric C18-Sphingosines and a Palmitoyl Analogue of Gaucher Spleen Glucocerebroside
- Synthesis of Methyl O-Acetyl-griseoluteate
- Studies on Phenazines. XXX. Bromination of Phenazine Derivatives by N-Bromosuccinimide. (2)
- Marine Natural Products. XXXII. Absolute Configurations of C-4 of the Manoalide Family, Biologically Active Sesterterpenes from the Marine Sponge Hyrtions erecta
- Marine Natural Products. XXXI. Structure-Activity Correlation of a Potent Cytotoxic Dimeric Macrolide Swinholide A, from the Okinawan Marine Sponge Theonella swinhoei, and Its Isomers
- ALTOHYRTINS B AND C AND 5-DESACETYLALTOHYRTIN A, POTENT CYTOTOXIC MACROLIDE CONGENERS OF ALTOHYRTIN A, FROM THE OKINAWAN MARINE SPONGE HYRTIOS ALTUM
- Indonesian Medicinal Plants. XI. Chemical Structures of Caesaldekarins a and b, Two New Cassane-Type Furanoditerpenes from the Roots of Caesalpinia major (Fabaceae)
- A NEW METHOD FOR MEASURING IONOPHORETIC ACTIVITY USING A GLASS-CELL APPARATUS EQUIPPED WITH ARTIFICIAL MEMBRANES
- ESCINS-Ia, Ib, IIa, IIb, AND IIIa, BIOACTIVE TRITERPENE OLIGOGLYCOSIDES FROM THE SEEDS OF AESCULUS HIPPOCASTANUM L. : THEIR INHIBITORY EFFECTS ON ETHANOL ABSORPTION AND HYPOGLYCEMIC ACTIVITY ON GLUCOSE TOLERANCE TEST
- Chemical Studies of Chinese Licorice-Roots. I. Elucidation of Five New Flavonoid Constituents from the Roots of Glycyrrhiza glabra L. Collected in Xinjiang
- ABSOLUTE STEREOSTRUCTURES OF PAEONISOTHUJONE, A NOVEL SKELETAL MONOTERPENE KETONE, AND DEOXYPAEONISUFFRONE, AND ISOPAEONISUFFRAL, TWO NEW MONOTERPENES, FROM MOUTAN CORTEX
- ABSOLUTE STEREOSTRUCTURES OF PAEONISUFFRONE AND PAEONISUFFRAL, TWO NEW LABILE MONOTERPENES, FROM CHINESE MOUTAN CORTEX
- Histochemistry. VI. Tocopherols and Isoflavones in Soybeans (Glycine max MERRILL, Seeds)
- Histochemistry. V. Soyasaponins in Soybeans (Glycine max MERRILL, Seeds)
- Indonesian Medicinal Plants. X. Chemical Structures of Four New Triterpene-Glycosides, Gongganosides D, E, F, and G, and Two Secoiridoid-Glucosides from the Bark of Bhesa paniculata (Celastraceae)
- Indonesian Medicinal Plants. IX. Chemical Structures of Gongganosides A, B, and C, Three New Quinovic Acid Glycosides from the Bark of Bhesa paniculata (Celastraceae)
- Marine Natural Products. XXX. Two New 3-Keto-4-methylene Steroids, Theonellasterone and Conicasterone, and a Diels-Alder Type Dimeric Steroid Bistheonellasterone, from the Okinawan Marine Sponge Theonella swinhoei
- Marine Natural Products. XXIX. Heterosigma-glycolipids I, II, III, and IV, Four Diacylglyceroglycolipids Possessing ω3-Polyunsaturated Fatty Acid Residues, from the Raphidopycean Dinoflagellate Heterosigma akashiwo
- On the Constituents of Picrorhiza kurrooa. (1). The Structure of Picroside I, a Bitter Principle of the Subterranean Part
- Saponin and Sapogenol. IV. Seeds Sapogenols of Aesculus turbinata BLUME. On the Configuration of Hydroxyl Functions in Ring E of Aescigenin, Protoaescigenin, and Isoaescigenin in Relation to Barringtogenol C and Theasapogenol A
- Saponin and Sapogenol. III. Seeds Sapogenols of Thea sinensis L. (3). Theasapogenol E and Minor Sapogenols
- Saponin and Sapogenol. II. Seeds Sapogenols of Thea sinensis L. (2). Theasapogenol A
- Saponin and Sapogenol. I. Seeds Sapogenols of Thea sinensis L. (1). Barringtogenol C (=Theasapogenol B)
- Comparative Study on the Sapogenin Constituents of Five Primulaceous Plants
- On the Iridoid Constituent isolated from the Roots of Scrophularia buergeriana MIQ.
- Lichen Triterpenoids. IV. The Structures of Leucotylic Acid and Methyl Isoleucotylate, an Acid-induced Isomer of Methyl Leucotylate
- On the Triterpenic Constituents of a Lichen, Parmelia entotheiochroa HUE.; Zeorin, Leucotylin, Leucotylic Acid, and Five New Related Triterpenoids
- Saponin and Sapogenol. XXII. Structure of Spergulatriol, A New Bisnorhopane-type Genuine Sapogenol of Isoanhydrospergulatriol, from the Root of Mollugo spergula L.
- Soil Bacterial Hydrolysis leading to Genuine Aglycone. X. On the Structure of a Genuine Sapogenol of Meteogenin, an A-Ring Aromatized Spirostanol from Metanarthecium luteo-viride MAXIM.
- On the Constituents of Seeds of Horsfieldia iryaghedhi WARB. I
- Lichen Triterpenoids. III. The Final Conclusion on the Stereostructure of Zeorin and Its Correlation with Leucotylin. The Structure of Isoleucotylin
- Lichen Triterpenoids. II. The Stereostructure of Zeorin
- Lichen Triterpenoids. I. The Structure of Leucotylin
- Structure of a Lichen Pigment Entothein and Its Identity with Secalonic Acid A, a Major Ergot Pigment
- The Chemical Proof of Hopane Skeleton of Zeorin
- Coloring Substances of a Lichen Cetraria ornata
- Skyrin from Two Lichen Species
- Soil Bacterial Hydrolysis leading to Genuine Aglycone. VII. On Monoterpenoid Glucosides of Scrophularia buergeriana MIQ. and Paeonia albiflora PALLAS
- プロトポルフィリン(IX)およびその関連化合物の研究(第1報) : ヘミンから純粋なプロトポルフィリン(IX)の生成
- Partial Synthesis of Priverogenin B from Camelliagenin A
- Saponin and Sapogenol. X. Structures of Jegosapogenin and Desacyljegosaponin obtained from Pericarps of Styrax japonica SIEB. et ZUCC.
- Revised Structure of Desacyl-jegosaponin
- Structure of Desacyl-jegosaponin, a Common Desacyl Derivatives of Jegosaponin isolated from Pericarps of Styrax japonica SIEB. et ZUCC.
- Structure of Hinesol
- Studies on the Constituents of Atractylodes. VIII. : The Structure of Atractylodin. (3). : Synthesis.
- Studies on the Constituents of Atractylodes. VII. : The Structure of Atractylodin. (2). : The Chromophores.
- Studies on the Constituents of Atractylodes. VI. : The Structure of Atractylodin. (1). : The Skeleton.
- 23.茅蒼朮の精油成分Hinesolの構造
- Studies on the Constituents of Atractylodes. IV. The Structure of Hinesol. (1). The Skeleton
- 22.東北大個求の精油成分atractylinの構造
- Studies on the Constituents of Atractylodes. III. Separation of Atractylol into Eudesmol and Hinesol.
- The Structure of Constictic Acid
- Lichen Triterpenoids. V. On the Neutral Triterpenoids of Pyxine endochrysina NYL.
- Urine Data Analysis for Pharmacokinetics of Acetanilide Hydroxylation in Man
- Biogenetically Patterned Transformation of Eudesmanolide to Eremophilanolide. I. Angular Methyl Migration of 5α, 6α-Epoxy-dihydroalantolactone
- Vittatolic Acid, a New Depsidone Isolated from the Lichen Hypogymnia vittata (ACH.) GAS.
- Saponin and Sapogenol. XVII. Structure of Sakuraso-saponin, a Pentaglycoside of Protoprimulagenin A from the Root of Primula sieboldi E. MORREN
- The Structure of Caloploicin, a New Lichen Trichloro-depsidone
- A New Trichloro-depsidone from a Lichen of the Genus Caloplaca
- Diacetyl-atractylodiol, a New Acetylenic Compound from Atractylodes japonica KOIDZUMI
- Saponin and Sapogenol. V. Sapogenol Constituents of Seeds of Camellia sasanqua THUNB. and Leaves of Ternstroemia japonica THUNB.
- Soil Bacterial Hydrolysis leading to Genuine Aglycone. V. On Ginsenosides-Rb_1,Rb_2,and Rc of the Ginseng Root Saponins
- Soil Bacterial Hydrolysis leading to Genuine Aglycone. IV. Four Acylated Derivatives of Barringtogenol C from Jegosaponin
- Saponin and Sapogenol. VI. Sapogenol Constituents of Leaves of Pittosporum tobira AIT.
- The Sapogenol Constituents of the Leaves of Pittosporum tobira AIT
- Saponin and Sapogenol. XXVII. Revised Structures of Holotoxin A and Holotoxin B, Two Antifungal Oligoglycosides from the Sea Cucumber Stichopus japonicus SELENKA
- Biogenetically Patterned Transformation of Eudesmanolide to Eremo-philanolide. II. Structures of Minor Products obtained by Acid Treatment of 5α, 6α-Epoxy-eudesman-8β, 12-olide
- Biogenetically Patterned Transformation of Eudesmanolide to Eremophilanolide. III. Acid Treatment of 4α, 5α-Epoxy-eudesman-8β, 12-olide
- Studies on the Constituents of Atractylodes. IX. Structure and Autoxidation of Atractylon
- Structure and Autoxidation of Atractylon
- Saponin and Sapogenol. VII. Sapogenol Constituents of Five Primulaceous Plants
- The Structure and Absolute Configuration of Hinesol
- ポリアセチレン化合物の研究(第1報) : 高等植物における分布 その1 マメ科, ウコギ科, セリ科, ミズキ科について
- Studies on the Constituents of Atractylodes. X. Correlation of Hinesol and β-Vetivone
- 23.Hinesolよりβ-Vetivone enantiomerへの変換
- On the Constituents of Linaria japonica MIQ. II. The Structure of Linaridial, a New cis-Clerodane-type Diterpene Dialdehyde
- Saponin and Sapogenol. XIV. Antifugal Glycosides from the Sea Cucumber Stichopus japonicus SELENKA. (1). Structure of Stichopogenin A_4,the Genuine Aglycone of Holotoxin A
- Saponin and Sapogenol. XVI. Structure of Desacyl-boninsaponin A obtained from the Bark of Schima mertensiana KOIDZ.
- Saponin and Sapogenol. VIII. Photochemical Cleavage of Glycoside Linkage in Saponin. (1). Photolysis of Some Saponins and Their Structural Features
- Saponin and Sapogenol. XV. Antifungal Glycosides from the Sea Cucumber Stichopus japonicus SELENKA. (2). Structures of Holotoxin A and Holotoxin B
- Stereostructures of Decursin, Decursidin, and a New Coumarin Isolated from Angelica decursiva
- A New Depsidone Oxyphysodic Acid isolated from a Lichen Parmelia enteromorpha ACH.
- 11-O-Galactosyl-nogiragenin, a Prosapogenol of Metanarthecium luteo-viride MAXIM. obtained by Soil Bacterial Hydrolysis
- Saponin and Sapogenol. IX. Structure of Spergulagenin A, a New Migrated Hopane-type Sapogenol isolated from Mollugo spergula L.
- Saponin and Sapogenol. XI. Chemical Correlation of Spergulagenin A, a New Migrated Hopane-type Sapogenol, with Hydroxyhopane
- Protobassic Acid, a Genuine Sapogenol of Seed Kernels of Madhuca longifolia L.
- Saponin and Sapogenol. XII. Mi-Saponin A and Mi-Saponin B, Two Major Bisdesmosides from the Seed Kernels of Madhuca longifolia (L.) MACBRIDE
- On the Constituents of Linaria japonica MIQ. I. The Structure of Linarioside, a New Chlorinated Iridoid Glucoside and Identification of Two Related Glucosides
- The Sapogenin Constituent of the Seeds of Camellia sasanqua THUNB
- On the Triterpenic Constituents of the Seeds Saponin of Aesculus turbinata BLUME