42 ヒカゲノカズラ中の16-Oxoserratene系トリテルペノイド
スポンサーリンク
概要
- 論文の詳細を見る
Five triterpenoids containing conjugated ketone chromophor were newly isolated-four (A, B, C, and E) from L. clavatum and one (D) from L. serratum, -and characterized. Their structures and stereochemistry were elucidated as 16-oxodiepiserratenediol (1), 16-oxoepiserratenediol (2), 16-oxoserratenediol (3), 16-oxoserratriol (4), and 16-oxolycoclavanol(5), respectively, based on spectroscopic and chemical evidence, wherein several new methods in solving the structural and steric problems were discussed: i.e., i) Application of TH-effect, ii) NMR classification of acetonide types, iii) Alkaline treatment and LAH reduction of 23 or 24-monotosylate. Particularly, the last method had a great advantage to elucidate the stereochemistry of substituents at ring A of poly-hydroxylated triterpenoid by noticing the key-product, an oxetane (18) or a seco-compound (20). 3-Keto-23 or 24-tosylate, (23) and (24), on treatment with t-BuOK, gave novel cyclobutanone derivatives, (25) and (26), which showed strong positive and negative Cotton effect corresponding to its stereochemistry, thus giving a new chemical method for determination of the position of tosyloxy group.
- 天然有機化合物討論会の論文
- 1968-09-20
著者
-
津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
-
森本 明
Showa College Of Pharmaceutical Sciences
-
藤本 琢憲
Showa College of Pharmaceutical Sciences
-
津田 喜典
昭和薬大
-
藤本 琢憲
昭和薬大
-
森本 明
阪大薬
関連論文
- Studies on Crude Drugs Effective on Visceral Larva Migrans. IV. : Isolation and Identification of Larvicidal Principles in Pepper
- Studies on Crude Drugs Effective on Visceral Larva Migrans. III. : The Bursting Activity of Tannins on Dog Roundworm Larva
- Studies on Crude Drugs Effective on Visceral Larva Migrans. II. : Larvicidal Principles in Kaempferiae Rhizoma
- A Convenient Synthesis of Tertiary Amines by Alkylation of Secondary Amines with Alkyl Halides in the Presence of Potassium Hydride and Triethylamine
- Stereoselective Introduction of Oxygen Functionalities at the 11β-Position of Erythrinan Skeleton : Total Syntheses of (±)-Erythristemine and (+)-Erythrartine
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (5). Cyclization of Perhydro-2-epoxymethylene-6-oxo-6H-pyrido[2,1-i]indole-1-acetic Acid : Synthesis of 8-Oxoerythroidans
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids.(3). Synthesis of β-Erythroidine Skeleton (β-Erythroidan)
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (1). Synthesis and Isomerization of Unsaturated Bicyclic δ-Lactones
- Mobility Inhibition and Nematocidal Activity of Asarone and Related Phenylpropanoids on Second-Stage Larvae of Toxocara canis
- Nematocidal Activity of Turmeric : Synergistic Action of Curcuminoids
- Nematocidal Activity of Long Alkyl Chain Amides, Amines, and Their Derivatives on Dog Roundworm Larvae
- Nematocidal Principles in "Oakmoss Absolute" and Nematocidal Activity of 2,4-Dihydroxybenzoates
- Studies on Crude Drugs Effective on Visceral Larva Migrans. V. : The Larvicidal Principle in Mace (Aril of Myristica fragrans)
- Chiral Synthesis of Erythrina Alkaloids. (2). Synthesis of enantio-Type Erythrinan Alkaloids Utilizing Asymmetric Acylation and Kinetic Resolution of Diastereomers
- CHIRAL SYNTHESIS OF ENANTIO-TYPE ERYTHRINAN ALKALOIDS UTILIZING ASYMMETRIC ACYLATION AND KINETIC RESOLUTION OF DIASTEREOMERS
- 4,4-Dimethyl Effect. (7). The A-Ring Conformation of 4,4-Dimethyl-3-keto Steroids in Solution. The Circular Dichroism Spectra of Onoceranediones
- 4,4-Dimethyl Effect (2). Syntheses, ^1H- and ^C-Nuclear Magnetic Resonance Spectra, and the Conformations of 6α- and 6β-Substituted-1,1,10β-trimethyl-trans-decal-2-ones (8α- and 8β-Substituted-4,4,10β-trimethyl-trans-decal-3-ones), Models of 4,4-Dimet
- Barbaloin Stimulates Growth of Eubacterium sp. Strain BAR, a Barbaloin-Metabolizing Bacterium from Human Feces
- 4,4-Dimethyl Effect. (3). The Ring A Conformation of 4,4-Dimethyl-Δ^7-3-keto Steroids and 4,4,8-β-Trimethyl-3-keto Steroids (3-Keto-triterpenoids). The Crystal Structure of Serratenedione
- SYNTHESES OF THE β-ERYTHROIDINE SKELETON(Communications to the Editor)
- ASYMMETRIC [2+2] PHOTOCYCLOADDITION REACTION OF A CHIRAL DIOXOPYRROLINE TO 2-(TRIMETHYLSILYLOXY)BUTADIENE : CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS
- A Stable Monosubstituted Isoindole Derivative : The Crystal Structure of 1-(1,2,3-1H-Benzotriazol-1-yl)-2-(4-methylphenyl)-2H-isoindole
- REARRANGEMENT OF 2,3-DIOXO-1,4-OXAZINES TO 4,5-DIOXOOXAZOLES IN THE REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE
- Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
- Synthesis of Highly Deydrogenated Oxoerythrinan Alkaloids, Erytharbine and Crystamidine
- Dioxypyrrolines. LV. Stereochemical Pathway of [2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes
- Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions
- Dioxopyrroline. LIV. Steretchemical Pathway of[2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Acyclic Olefins
- Dioxopyrrolines. LIII.Stereochemical Pathway of [2+2] Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers
- Reaction of Phenylselenenyl Chloride with Δ^2-Erythrinans in Methanol : Conformational Fluctuation and Stereochemical Pathway
- Hydride Reduction of Erythrinan-7,8-diones and 7-O-Methanesulfonyl-8-oxo-erythrinans
- Synthesis and Reactions of 3,7-Cycloerythrinan : Skeletal Rearrangement of 2,7,8-Trioxoerythrinans to 4-Oxo-4H-pyrido[2,1,-a]isoquinolines
- Synthesis of Erythrina and Related Alkaloids.XXIV. Total Synthesis of Erysotrine from 1,7-Cycloerythrinan Derivatives by the Use of a New 1,2-Carbonyl Transposition Method
- Synthesis of Erythrina and Related Alkaloids. XXIII. : Intramolecular Cyclization Approach. (2). Synthesis and Reactions of 1,7-Cyclo-cis-erythrinans, Potential Intermediates to Natural Erythrina Alkaloids
- Synthesis of Erythrina and Related Alkaloids. XXII. : Intramolecular Cyclization Approach. (1) : New Synthetic Route to Erythrinan and Related Heterocycles and Synthesis of (±)-3-Demethoxy-erythratidinone
- Photo-Cycloaddition of 3-Methoxycyclohexenone and 3-Aminocyclohexenone to Ethoxyethylene : Stereochemistry of the Cycloadducts
- Studies toward Total Synthesis of Non-aromatic Erythring Alkaloids. (6). Synthesis of 8-OXO-γ-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (4). Oxidation of Furan Ring of D-Furanoerythrinans with N-Bromoacetamide
- Regioselective Syntheses of Mono-O-acylglucoses
- SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD
- Regioselective Monotosylation of Non-protected and Partially Protected Glycosides by the Dibutyltin Oxide Method
- 4,4-Dimethyl Effect. (4). The Conformation of α-Onoceradienedione in the Crystalline State
- Photodecarboxylation of Arylacetic Acids
- Regioselective Introduction of a Methoxy Group at the Benzylic Position of Isochromane Derivatives by Cerium(IV) Oxidation in Methanol
- Dioxopyrrolines. XLIII. : Diels-Alder Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione with Butadienes : Synthesis of Polyfunctionalized Hydroindoles
- SYNTHESIS OF COCCULOLIDINE SKELETON, A NON-AROMATIC NOR-ERYTHRINAN ALKALOID(Communications to the Editor)
- Chemoselective Reduction of β-Keto esters to β-Keto-alcohols
- Triterpenoid Chemistry. VI. Lycopodium Triterpenoid. (5). The Structures and Stereochemistry of Serratriol, 21-Episerratriol, and Lycoclavanol
- 42 ヒカゲノカズラ中の16-Oxoserratene系トリテルペノイド
- Stereochemical Correlation of Di- and Trihydroxy-β-diketone Fungal Metabolites, (-)-Terredionol and Terremutin Hydrate, with Sugar Alcohols : The Absolute Configuration of (-)-Terredionol
- Studies on the Metabolic Products of Oospora astringenes. VIII. Isolation, Chemical Structure, and Biosynthesis of Oospolide
- REGIOSELECTIVE INTRODUCTION OF p-COUMAROYL GROUP TO α-L-ARABINO-PYRANOSIDES. TOTAL SYNTHESES OF INUNDOSIDE-G AND INUNDOSIDE-D_1
- Lycopodium Triterpenoids. (12). Syntheses of Inundoside-A and -E, Triterpenoid-glycosides of Lycopodium inundatum L.
- Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates
- Synthesis of Erythrina and Related Alkaloids. XXX. Photochemical Approach. (1). Synthesis of Key Intermediates to Erythrina Alkaloids by Intermolecular [2+2] Photocycloaddition Followed by 1,3-Shift
- Dioxopyrroline. L. Skeletal Rearrangements of 7-Vinyl-7-trimethylsilyloxy-5-ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones under Thermal, Basic, and Acidic Conditions
- Dioxopyrrolines. XLVII. : Thermal Rearrangements of 7-Vinyl Derivatives of 1-Aryl-5-ethoxy-carbonyl-2-azabicyclo[3.2.0]heptane-3,4-diones and Their Imidates
- Synthesis of Erythrina and Related Alkaloids. XVI. Diels-Alder Approach: Total Synthesis of dl-Erysotrine, dl-Erythraline, dl-Erysotramidine, dl-8-Oxoerythraline and Their 3-Epimers(Organic,Chemical)
- Dioxopyrrolines. XXXII. X-Ray Determination of the Molecular Structure of a Photoadduct of 2-Trimethylsilyloxybutadiene to 3-Ethoxycarbonyl-2-phenyl-Δ^2-pyrroline-4,5-dione
- Dioxopyrrolines. XXVII. Syntheses of 2-Aryl-3-ethoxycarbonyl-Δ^2-pyrroline-4,5-diones
- FACILE OXY-VINYL[1,3]SHIFT PROMOTED BY TETRABUTYLAMMONIUM FLUORIDE : A HYDROINDOLE SYNTHESIS
- FACTORS CONTROLLING C=C VS. C=O ATTACK IN CYCLOADDITION OF A 1,3-DIENE TO AN AMBIDENT DIENOPHILE. DIELS-ALDER REACTION OF 2-PHENYL-Δ^2-PYRROLINE-4,5-DIONES
- Stereoselective Transformation of the Alkaloid Lycorine to O-Demethylungiminorine and Ungiminorine
- Conversion of Thiocarbonyl into Carbonyl Group by O-S Exchange Reaction with Dibutyltin Oxide or Bistributyltin Oxide
- Total Synthesis of Hydroxyhopanone
- Dioxopyrrolines. XLIV. : Thermal 1,3-Shift of 2-Azabicyclo[3.2.0]hept-2-ene Ring System : A New Entry to 3,4-Dihydropyridines and 2-Azanorborn-2-enes
- Dioxopyrrolines.XLII. : Mechanism of 7-Epimerization Reaction of 7-Substituted 5-Ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones
- Dioxopyrrolines. XXXV. Synthesis of 2H-Azepin-2-ones (2-Azatropones)
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (2). A General Method for Synthesis of Perhydro-6H-pyrido[2,1-i]indole Derivatives : Synthesis of Isoerythroidine Skeleton
- Synthesis of Malabaricones, Diarylnonanoids Occurring in Myristicaceous Plants
- A NEW 1,2-CARBONYL TRANSPOSITION METHOD VIA PHENYLSELENENYLATION. HIGH YIELD TRANSFORMATION OF O-METHYLESTRONE TO O-METHYLISOESTRONE
- Dioxopyrrolines. XLIX. Synthesis of Azatropolones via Photocycloaddition of 5-Aryl-4-ethoxycarbonyl-1H-pyrrole-2,3-diones to Acetylenes and Ethylenes
- Dioxopyrrolines. XLVIII. : Regioselective Formation of Hydroindoles via Photochemical and Thermal Cycloaddition Reactions of 5-Aryl-4-ethoxycarbonyl-1H-pyrrole-2,3-dione with Isoprene
- Dioxopyrrolines. XLVI. : [2+2] Photocycloaddition of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Six-Membered Cycloolefins : Effect of Ring Size on Stereochemical Pathways
- Dixopyrrolines. XLV. : [2+2] photocycloaddition of 4-Ethoxycarbonyl-5-aryl-1H-pyrrole-2,3-dione to Cyclopentene Derivatives : Formation of Dihydropyridones
- Dioxopyrrolines. XLI. : X-Ray Crystallographic Determination of the Stereochemistry of an Azatricyclo[5.3.0.0^]decane Derivative Obtained by Photocycloaddition of Cyclopentadiene to 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione
- Dioxopyrrolines. XL. Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Dihydrofurans. Formation of a 2,4-Dioxa-10-azatricyclo[6.3.0.0^]undecane Ring System(Organic,Chemical)
- Dioxopyrrolines. XXXVII. Stereochemical Pathways of Dioxopyrroline-Olefin Pbotocycloaddition. Stereochemical Selection Rule for the Photocycloaddition of Enone-Olefin Pairs(Organic,Chemical)
- Dioxopyrrolines. XXXVI. [2+2] photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Acyclic Olefins. Structural and Stereochemical Assignment of the Photocycloadducts(Organic,Chemical)
- Dioxopyrrolines. XXIX. Solvolytic Behavior of 3-Ethoxycarbonyl-2-phenyl-Δ^2-pyrroline-4,5-diones in Protic Solvents
- Infrared Spectra of Conjugated Amides : Reassignment of the C=O and C=C Absorptions
- Lycopodium Triterpenoids. (7). The Structures and Partial Syntheses of 16-Oxoserratenediol, 16-Oxo-21-episerratenediol, 16-Oxodiepiserratenediol, 16-Oxoserratriol, 16-Oxo-21-episerratriol, and 16-Oxolycoclavanol, α, β-Unsaturated Ketones of Serratane Grou
- クミスクチンよりイノシトールの単離
- Trichothecium roseum LINKの代謝産物の研究Rosein IIIの構造
- Synthesis and Nematocidal Activity of Hydroxystilbenes
- Tazettine Chemistry. X. The Structure of Products obtained from O-Methyltazettine Methine Methosalts under the Hofmann Elimination Conditions.
- The Structure of Serratenediol.
- New Method for Isomerization of (Z)-Stilbenes into the (E)-Isomers Catalyzed by Diaryl Disulfide
- CHEMISTRY OF OXO-SUGARS (1). REARRANGEMENT OF 2-OXOGLYCOSIDES IN PYRIDINE : EVIDENCE OF INTRAMOLECULAR HYDRIDE SHIFT
- Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre
- TRIALKYLTIN RADICAL USED TO CATALYZE THE O,S-REARRANGEMENT OF CYCLIC THIONOCARBONATES. A NEW ENTRY TO THIO-SUGARS(Communication to the Editor)
- 21-Episerratenediol, Isolation and its Structure
- Lithium Aluminum Hydride Reduction of Glycopyranoside-Monosulfonates : Formation of Branched Furanosides
- TWO NEW GYMNEMIC ACID CONGENERS CONTAINING A HEXULOPYRANOSIDE MOIETY
- Z-E Isomerization of β-Methoxychalcones : Preferred Existence of E-Isomers in Naturally Occurring β-Methoxychalcones
- Regio- and Stereo-Selective Transformation of Glycosides to Amino-glycosides : Practical Synthesis of Amino-sugars, 4-Amino-4-deoxy-D-galactose, 4-Amino-4-deoxy-L-arabinose, 3-Amino-3-deoxy-D-allose, 3-Amino-3-deoxy-D-glucose, 3-Amino-3-deoxy-D-ribose, 3-
- Regioselective Mono-oxidation of Non-protected Carbohydrates by Brominolysis of the Tin Intermediates
- Selective Deoxygenation via Regioselective Thioacylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method(Organic,Chemical)
- Hexahydro-dibenz[d, f]azecines : Existence of Two Conformational Isomers of the 6-Oxo Derivatives in Solution
- Lycopodium Triterpenoids. (10). Triterpenoid Constituents of Lycopodium wightianum collected in Borneo