Chemical Transformation of Terpenoids. III. Syntheses of (3R)-1-Vinyl-, (3R)-1-Hydroxypropenyl-, and (3R)-1-Epoxyethyl-5-methoxy-1,2,2-trimethylcyclopentane Derivatives from d-Camphor via 5-Oxo-d-bornyl Acetate
スポンサーリンク
概要
- 論文の詳細を見る
As a continuation of our transformation studies on terpenoids, three optically active 5-methoxy-1,2,2-trimethylcyclopentane derivatives, i.e., (+)-(1R, 3R, 5S)-3-acetoxymethyl-5-methoxy-1,2,2-trimethyl-1-vinylcyclopentane (7), (+)-(1R, 3R, 5S)-3-acetoxymethyl-1-(3'-hydroxypropenyl)-5-methoxy-1,2,2-trimethylcyclopentane (8), and (-)-(1R, 3R, 5S, 1'R)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-5-methoxy-1,2,2-trimethylcyclopentane (9), were synthesized from d-camphor (1) via 5-oxo-d-bornyl acetate (6). All three compounds (7,8,9) retain the C-4 configuration of d-camphor at their C-3 positions.
- 社団法人日本薬学会の論文
- 1982-04-25
著者
-
北川 勲
Faculty of Pharmaceutical Sciences, Osaka University
-
山本 佳男
Faculty Of Pharmaceutical Sciences Osaka University
-
渋谷 博孝
Faculty of Pharmaceutical Sciences, Osaka University
-
藤岡 弘道
Faculty Of Pharmaceutical Sciences Osaka University
-
梶原 彰治
Faculty of Pharmaceutical Sciences, Osaka University
-
北川 勲
Faculty Of Pharmaceutical Sciences Osaka University
-
梶原 彰治
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)
- 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
- 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
- ARAGUSPONGINES B, C, D, E, F, G, H, AND J, NEW VASODILATIVE BIS-1-OXAQUINOLIZIDINE ALKALOIDS FROM AN OKINAWAN MARINE SPONGE, XESTOSPONGIA SP.
- Chemical Transformation of Terpenoids. VI. Syntheses of Chiral Segments, Key Building-Blocks for the Left Half of Taxane-Type Diterpenoids
- Chemical Transformation of Terpenoids. IV. Acid Treatment of (3R)-1-Vinyl-, (3R)-1-Hydroxypropenyl-, and (3R)-1-Epoxyethyl-5-methoxy-1,2,2-trimethylcyclopentane Derivatives : Ring Enlargement Reactions and Successive Migrations of Methyl Residues
- Chemical Transformation of Terpenoids. III. Syntheses of (3R)-1-Vinyl-, (3R)-1-Hydroxypropenyl-, and (3R)-1-Epoxyethyl-5-methoxy-1,2,2-trimethylcyclopentane Derivatives from d-Camphor via 5-Oxo-d-bornyl Acetate
- Chemical Transformation of Terpenoids. II. Acid Treatment of (3S)-1-Vinyl-, (3S)-1-Hydroxypropenyl-, and (3S)-1-Epoxyethyl-1,2,2-trimethylcyclopentane Derivatives : Ring Enlargement Reactions and Successive Migrations of Methyl Residues
- Chemical Transformation of Terpenoids. I. Syntheses of (3S)-1-Vinyl-, (3S)-1-Hydroxypropenyl-, and (3S)-1-Epoxyethyl-1,2,2-trimethylcyclopentane Derivatives from d-Camphor via d-Camphoric Acid
- Biogenetically Patterned Transformation of Eudesmanolide to Eremophilanolide. V. Studies on Stereochemical Factors for Favorable Conversion of 5α, 6α-Epoxy-eudesman-8β, 12-olide leading to Eremophilane-type Derivatives
- 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.
- Marine Natural Products. XXXIV. Trisindoline, a New Antibiotic Indole Trimer, Produced by a Bacterium of Vibrio sp. Separated from the Marine Sponge Hyrtios altum
- Indonesian Medicinal Plants. VI. On the Chemical Constituents of the Bark of Picrasma javanica BL. (Simaroubaceae) from Flores Island. Absolute Stereostructures of Picrajavanins A and B
- Marine Natural Products. X. Pharmacologically Active Glycolipids from the Okinawan Marine Sponge Phyllospongia foliascens (PALLAS)
- Foliaspongin, an Antiinflammatory Bishomosesterterpene from the Marine Sponge Phyllospongia foliascens (PALLAS)
- Studies on the chemical Modification of Monensin. III. Synthesis and Sodium Ion transport Activity of macrocylic Monenslamino Acid-1,29-lactones
- DEHATRINE, AN ANTIMALARIAL BISBENZYLISOQUINOLINE ALKALOID FROM THE INDONESIAN MEDICINAL PLANT BEILSCHMIEDIA MADANG, ISOLATED AS A MIXTURE OF TWO ROTATIONAL ISOMERS
- Solubilization of Saponins of Bupleuri Radix with Ginseng Saponins : Effect of Malonyl-ginsenosides on Water Solubility of Saikosaponin-b
- Indonesian Medicinal Plants. V. Chemical Structures of Calotroposides C, D, E, F, and G, Five Additional New Oxypregnane-Oligoglycosides from the Root of Calotropis gigantea (Asclepiadaceae)
- Indonesian Medicinal Plants. IV. On the Constituents of the Bark of Fagara rhetza (Rutaceae). (2). Lignan Glycosides and Two Apioglucosides
- Indonesian Medicinal Plants. III. On the Constituents of the Bark of Fagara rhetza (Rutaceae).(1) : Alkaloids, Phenylpropanoids, and Acid Amide
- Indonesian Medicinal Plants. II. Chemical Structures of Pongapinones A and B, Two New Phenylpropanoids from the Bark of Pongamia pinnata (Papilionaceae)
- Indonesian Medicinal Plants. I. Chemical Structures of Calotroposides A and B, Two New Oxypregnane-Oligoglycosides from the Root of Calotropis gigantea (Asclepiadaceae)
- Three New Oleanene Glycosides from Sophora flavescens
- GALLOYL-OXYPAEONIFLORIN, SUFFRUTICOSIDES A, B, C, AND D, FIVE NEW ANTIOXIDATIVE GLYCOSIDES, AND SUFFRUTICOSIDE E, A PAEONOL GLYCOSIDE, FROM CHINESE MOUTAN CORTEX
- Asernestioside C, a New Minor Saponin from the Roots of Astragalus ernestii COMB.; First Example of Negative Nuclear Overhauser Effect in the Saponins
- HETEROSIGMA-GLYCOLIPIDS I AND II, TWO NEW GALACTOLIPIDS CONTAINING OCTADECATETRAENOYL AND EICOSAPENTAENOYL RESIDUES, FROM A RAPHIDOPHYTE DINOFLAGELLATE HETEROSIGMA SP.
- Marine Natural Products. XX. : Bioactive Scalarane-Type Bishomosesterterpenes from the Okinawan Marine Sponge Phyllospongia foliascens
- Marine Natural Products. XIX. : Pervicosides A, B, and C, Lanostane-Type Triterpene-Oligoglycoside Sulfates from the Sea Cucumber Holothuria pervicax
- Marine Natural Products. XVIII. : Four Lanostane-Type Triterpene Oligoglycosides, Bivittosides A, B, C, and D, from the Okinawan Sea Cucumber Bohadschia bivittata MITSUKURI
- Marine Natural Products. XVII. Nephtheoxydiol, a New Cytotoxic Hydroperoxy-Germacrane Sesquiterpene, and Related Sesquiterpenoids from an Okinawan Soft Coral of Nephthea sp. (Nephtheidae)(Organic,Chemical)
- Marine Natural Products. XVI. : Structures of Five New Diterpenes from an Okinawan Soft Coral of Xenia sp. (Xeniidae)
- KERICEMBRENOLIDES A, B, C, D, AND E, FIVE NEW CYTOTOXIC CEMBRENOLIDES FROM THE OKINAWAN SOFT CORAL CLAVULARIA KOELLIKERI
- Marine Natural Products. XIV. Structures of Echinosides A and B, Antifungal Lanostane-Oligosides from the Sea Cucumber Actinopyga echinites (JAEGER)
- XENIOLONE AND ISOXENIOLONE TWO NEW DITERPENES HAVING A PERHYDROAZULENE SKELETON FROM AN OKINAWAN SOFT CORAL OF XENIA SP.
- HALENAQUINOL AND HALENAQUINOL SULFATE, PENTACYCLIC HYDROQUINONES FROM THE OKINAWAN MARINE SPONGE XESTOSPONGIA SAPRA
- CLAVUKERIN C, A NEW TRINOR-GUAIANE SESQUITERPENE HAVING A HYDROPEROXY FUNCTION, FROM THE OKINAWAN SOFT CORAL CLAVULARIA KOELLIKERI
- Marine Natural Products. XII. On the Chemical Constituents of the Okinawan Marine Sponge Hymeniacidon aldis
- CLAVUKERIN A, A NEW TRINOR-GUAIANE SESQUITERPENE FROM THE OKINAWAN SOFT CORAL CLAVULARIA KOELLIKERI
- ABSOLUTE STEREOSTRUCTURES OF CLAVIRIDENONE-A, -B, -C, AND -D FOUR PROSTANOIDS FROM THE OKINAWAN SOFT CORAL CLAVULARIA VIRIDIS
- THREE NEW ent-VALERENANE SESQUITERPENES FROM AN OKINAWAN SOFT CORAL
- Marine Natural Products. IX. Structural Elucidation of Triterpenoidal Oligoglycosides from the Bahamean Sea Cucumber Actinopyga agassizi SELENKA
- The Structures of Six Antifungal Oligoglycosides, Stichlorosides A_1,A_2,B_1,B_2,C_1,and C_2,from the Sea Cucumber Stichopus Chloronotus (BRANDT)
- Marine Natural Products. VIII. Bioactive Triterpene-Oligoglycosides from the Sea Cucumber Holothuria leucospilota BRANDT (2). Structure of Holethurin A
- Marine Natural Products. VII. Bioactive Triterpene-Oligoglycosides from the Sea Cucumber Holothuria leucospilota BRANDT (1). Structure of Holothurin B
- 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
- Marine Natural Products. XXVI. Biologically Active Tridecapeptide Lactones from the Okinawan Marine Sponge Theonella swinhoei(Theonellidae).(2).Structures of Theonellapeptolides Ia, Ib, Ic, and Ie
- Saponin and Sapogenol. XXX. Furostanol Glycosides from Metanarthecium luteo-viride MAXIM. : Bisdesmosides of Furometagenin and Furometanarthogenin
- Saponin and Sapogenol. XXII. Structure of Spergulatriol, A New Bisnorhopane-type Genuine Sapogenol of Isoanhydrospergulatriol, from the Root of Mollugo spergula L.
- 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
- Marine Natural Products. XXXIII. Theonellapeptolide IId, a New Tridecapeptide Lactone from the Okinawan Marine Sponge Theonella swinhoei
- Formation and Hydrolysis of Enamine in Aqueous Solution
- Saponin and Sapogenol. L. On the Constituents of the Roots of Glycyrrhiza uralensis FISCHER from Xinjiang, China. Chemical Structures of Licorice-Saponin L3 and Isoliquiritin Apioside
- LICORICE-SAPONINS F3,G2,H2,J2,AND K2,FIVE NEW OLEANENE-TRITERPENE OLIGOGLYCOSIDES FROM THE ROOT OF GLYCYRRHIZA URALENSIS
- Coloring Substances of a Lichen Cetraria ornata
- Skyrin from Two Lichen Species
- Saponin and Sapogenol. XLIX. On the Constitutents of the Roots of Glycyrrhiza inflata BATALIN from Xinjiang, China. Characterization of Two Sweet Oleanane-Type Triterpene Oligoglycosides, Apioglycyrrhizin and Araboglycyrrhizin
- Saponin and Sapogenol. XLVIII. On the Constituents of the Roots of Glycyrrhiza uralensis FISCHER from Northeastern China. (2).Licorice-saponins D3,E2,F3,G2,H2,J2,and K2
- Sphingolipids and Glycerolipids. I. : Chemical Structures and Ionophoretic Activities of Soyacerebrosides I and II from Soybean
- MAMMOSIDES B AND H1,NEW IONOPHORIC RESIN-GLYCOSIDES FROM THE TUBER OF MERREMIA MAMMOSA, AN INDONESIAN FOLK MEDICINE
- APIOGLYCYRRHIZIN AND ARABOGLYCYRRHIZIN, TWO NEW SWEET OLEANENE-TYPE TRITERPENE OLIGOGLYCOSIDES FROM THE ROOT OF GLYCYRRHIZA INFLATA
- LICORICE-SAPONINS A3,B2,C2,D3,AND E2,FIVE NEW OLEANENE-TYPE TRITERPENE OLIGOGLYCOSIDES FROM CHINESE GLYCYRRHIZAE RADIX
- Soil Bacterial Hydrolysis leading to Genuine Aglycone. VII. On Monoterpenoid Glucosides of Scrophularia buergeriana MIQ. and Paeonia albiflora PALLAS
- Sphingolipids and Glycerolipids. IV. Syntheses and Ionophoretic Activities of Several Analogues of Soya-cerebroside II, a Calcium Ionophoretic Sphingoglycolipid Isolated from Soybean
- Chemical Studies on Crude Drug Processing. VIII. On the Constituents of Rehmanniae Radix. (2) : Absolute Stereostructures of Rehmaglutin C and Glutinoside Isolated from Chinese Rehmanniae Radix, the Dried Root of Rehmannia glutinosa LIBOSCH.
- Saponin and Sapogenol. XLVII.On the Constituents of the Roots of Glycyrrhiza uralensis FISCHER from Northeastern China. (1). Licorice-Saponins A3,B2,and C2
- Chemical Studies on Crude Drug Processing. VII. On the Constituents of Rehmanniae Radix. (1) : Absolute Stereostructures of Rehmaglutins A, B, and D Isolated from Chinese Rehmanniae Radix, the Dried Root of Rehmannia glutinosa LIBOSCH.