The C(1)-C(10) bond cleavage and B ring aromatization of some 6-hydroxy-5.BETA.H-abieta-6,8,11,13-tetraen-18-oic acid 18,6-lactones.

スポンサーリンク

概要

• 論文の詳細を見る

• Fusion of 6-hydroxy-5β<I>H</I>-abieta-6,8,11,13-tetraen-18-oic acid 18,6-lactone (<B>2</B>) with potassium hydrogensulfate at 220 °C afforded bis[3-(2,3-dihydro-7-isopropyl-3,4-dimethyl-2-oxonaphtho[2,3-<I>b</I>]furan-3-yl)propyl] ether (<B>12</B>) in 37% yield, together with two minor products in 12% yield: 2,3-dihydro-7-isopropyl-3,4-dimethyl-3-propylnaphtho[2,3-<I>b</I>]furan-2-one and 3-allyl-2,3-dihydro-7-isopropyl-3,4-dimethylnaphtho[2,3-<I>b</I>]furan-2-one. Treatment of <B>12</B> with <I>p</I>-toluenesulfonic acid at 160 °C gave 2,3-dihydro-7-isopropyl-3,4-dimethyl-3-(3-tosyloxypropyl)naphtho[2,3-<I>b</I>]furan-2-one, which was converted into 2,3-dihydro-3-(3-hydroxypropyl)-7-isopropyl-3,4-dimethylnaphtho[2,3-<I>b</I>]furan-2-one (<B>16</B>). The alcohol <B>16</B> was further characterized as its acetate (<B>17</B>). After several attempts, the above C(1)–C(10) bond cleavage and B ring aromatization reaction were improved by use of concentrated sulfuric acid in refluxing acetic acid. Under these conditions, <B>2</B> gave <B>17</B> in 47% yield. Hydrolysis of <B>17</B> with hydrochloric acid afforded <B>16</B>. Subsequently, 12-hydroxy-, 12-methoxy-, 12-acetoxy-, and 12-nitro-6-hydroxy-5β<I>H</I>-abieta-6,8,11,13-tetraen-18-oic acid 18,6-lactones were each refluxed with concentrated sulfuric acid in acetic acid to give 6-hydroxy-, 6-methoxy-, 6-acetoxy-, and 6-nitro-3-(3-acetoxypropyl)-2,3-dihydro-7-isopropyl-3,4-dimethylnaphtho[2,3-<I>b</I>]furan-2-ones, respectively. From the present study, the 12-acetoxy derivative seems to be a suitable intermediate for the synthesis of coleon A.

• 公益社団法人 日本化学会の論文

著者

• YAMAMOTO Yasuhiro

  Department of Chemistry, Faculty of Science, Toho University

• Fukui Kenji

  Department Of Chemistry Faculty Of Science Hiroshima University

• Kataoka Hideo

  Deparment of Pathology, Shiga University of Medical Science, School of Medicine

• Imai Sachihiko

  Department of Chemistry, Faculty of Science, Hiroshima University

• Kataoka Hideo

  Department of Chemistry, Faculty of Science, Hiroshima University

• Takeyama Nobuaki

  Department of Chemistry, Faculty of Science, Hiroshima University

• Matsumoto Takashi

  Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima

• Ondo Kenji

  Department of Chemistry, Faculty of Science, Hiroshima University

• Matsumoto Takashi

  Department of Applied Material Science, Faculty of Integrated Arts and Science, University of Tokushima

関連論文

• Usefulness of procalcitonin serum level for the discrimination of severe sepsis from sepsis : a multicenter prospective study
• Synthesis and Characterization of (μ-Alkoxo)bis(μ-carboxylato)diruthenium Complexes, Na[Ru_2(dhpta)(μ-O_2CR)_2] (dhptaH_5 = 1,3-diamino-2-hydroxypropane tetraacetic acid). A Ruthenium Analogue of Model Systems for Iron-oxo Proteins
• Multicenter prospective study of procalcitonin as an indicator of sepsis
• 194. Equilibrium Function in Abnormal Varieties of Posture,Especially in Scoliosis
• Changes of lysosomal enzyme activity in aorta in spontaneously hypertensive rats (SHR).
• The effect of aromatherapy massage on mild depression : A pilot study
• IA-07 Spatiotemporal patterns of expression of IGSF4 in developing mouse nervous system(THE 46TH ANNUAL MEETING OF THE JAPAN SOCIETY OF HISTOCHEMISTRY AND CYTOCHEMISTRY)
• アルツハイマー病における自殺の社会心理的背景 : 日米アルツハイマー病患者2症例の比較ケーススタディ
• IS-84 A study on the changes in the vaginal environment depending on the life stages of females from the perspective of vaginal secretion cultures(Group10 Women's Health2,International Session)
• Men's Health Study : Epidemiology of Erectile Dysfunction and Cardiovascular Disease
• Correlation of Glomerular Permeability, Endothelial Injury, and Postoperative Multiple Organ Dysfunction
• Effects of angiotensin-converting enzyme inhibitor and α1-adrenoceptor antagonist on hypertension induced in rats by long-term inhibition of nitric oxide production
• 巨大インスリノーマのあった多内分泌腺腫症1型の1例
• Hyperthyroidism in a Patient with TSH-Producing Pituitary Adenoma Coexisting with Thyroid Papillary Adenocarcinoma
• Bilateral Traumatic Abducens Nerve Palsy Associated With Skull Base Fracture : Case Report
• Increased Regional Interleukin-4 During the Acute Stage of Severe Intracranial Disorders
• Paralytic Ileus Occurring during Treatment with All-trans Retinoic Acid for Acute Promyelocytic Leukemia
• BIOLOGICAL MONITORING OF METABOLITES OF SARIN AND ITS BY-PRODUCTS IN HUMAN URINE SAMPLES
• Low-Temperature Epitaxial Growth of CeO_2(110)/Si(100) Structure by Evaporation under Substrate Bias
• Analysis of Misoriented Crystal Structure by Ion Channeling Observed Using Ion-Induced Secondary Electrons
• Morphometric investigation of the hippocampal formation in Ihara's genetically epileptic rats using magnetic resonance images and histopathology
• Coexistence of Graves' Disease and Struma Ovarii: Case Report and Literature Review
• A Case of Primary Hyperparathyroidism Accompanying Multiple Myeloma
• The Tomato Photomorphogenetic Mutant, aurea, is Deficient in Phytochromobilin Synthase for Phytochrome Chromophore Biosynthesis
• Cerebral Endothelial Injury in Elderly Patients With Severe Head Injury Measured by Serum Thrombomodulin and von Willebrand Factor
• Linewidth of NMR Spectrum in Diluted Magnetic Systems
• High-Sensitivity Channeling Analysis of Lattice Disorder Near Surfaces Using Secondary Electrons Induced by Fast Ions
• Effect of Institutional Smoking Prohibition on Japanese Inpatients with Chronic Schizophrenia
• Frontotemporal dementia complicated with schizophrenia
• Anosognosia in Alzheimer's disease : Association with patient characteristics, psychiatric symptoms and cognitive deficits
• A Case of Prolonged Alcohol Withdrawal Syndrome Accompanied with Hyperthyroidsim
• Neurobehavioral changes associated with bilateral caudate nucleus infarctions
• Cerebral blood flow changes in general paresis following penicillin treatment : A longitudinal single photon emission computed tomography study
• Relationship between clock drawing test performance and regional cerebral blood flow in Alzheimer's disease : A single photon emission computed tomography study
• Qualitative analyses of clock drawings in Alzheimer's disease and vascular dementia
• Relationship between regional cerebral blood flow and verbal fluency in Alzheimer's disease
• Normotensive Bilateral Pheochromocytoma with Lindau Disease : Case Report
• Electrical Characteristics of Metal/Cerium Dioxide/Silicon Structures
• Japanese version of the Body Attitude Test : Its reliability and validity
• A behavior therapy program combined with liquid nutrition designed for anorexia nervosa
• Pharmacokinetics of Midazolam in Critically Ill Patients Receiving Continuous Hemodiafiltration using a Polymethyl Methacrylate and/or Polysulfone Membrane
• Differentiation of Adipose-derived Stromal Vascular Fraction Culture Cells into Chondrocytes Using the Method of Cell Sorting with a Mesenchymal Stem Cell Marker
• Enhanced expression of platelet-derived growth factor (PDGF) B-chain and its β-receptor in focal ischemia in rat brain
• Environmental factors involved in axonal regeneration following spinal cord transection in rats
• Immediate Postoperative Angiographic Embolization After Damage Control Surgery for Liver Injury : Report of a Case
• Regional cerebral blood flow in delirium patients
• Prevalence of primary aldosteronism among prehypertensive and stage 1 hypertensive subjects
• Myeloid Sarcoma in the Nasal Cavities that Developed during the Course of Acute Myelomonocytic Leukemia
• Recurrent primary cutaneous large B-cell lymphoma after a long-term remission
• Multiple Myeloma with a Variant Burkitt-type Translocation, t(2;8)(p12;q24), Associated with Hyperammonemia
• Superior Clinical Impact of FDG-PET Compared to MRI for the Follow-up of a Patient with Sacral Lymphoma
• Conformation Analysis of Organic Molecules by Modified Force Field Method
• Paternal overprotection in obsessive-compulsive disorder and depression with obsessive traits
• Reconstruction of the Tragus Using a Pedicled Chondrocutaneous Flap
• D-9-2 The Total Synthesis of Nepseudin(Phenolics)
• FACTORS PRODUCING VARIOUS RESPONSES TO ACETYLCHOLINE IN DOG HEPATIC CIRCULATION
• Expression and Localization of TRK-Fused Gene Products in the Rat Brain and Retina
• A p53 Gene Mutation in Malignant Fibrous Histiocytoma Associated with Bone Infarction
• Collins oxidation of methyl (+)-13.BETA.-abiet-8-en-18-oate and absolute configuration of suaveolic acid.
• Synthetic Studies of the Flavone Derivatives. III. The Synthesis of 3,7-Dimethoxy-5,6;3′,4′-bismethylenedioxyflavone, an Isomer of Meliternatin
• Analysis of Cellular Dynamics of SHRSP Aortic Endothelial Cells Monolayer Specimens
• Expression of nitric oxide synthase in astrocytes in the brain of stroke-prone spontaneously hypertensive rats
• Elastase in Aorta in SHR-SP
• Lysosomal enzyme activity in the arterial system in SHRSP:Acid phosphatase activity
• Histochemical study on lysosomal enzyme activities in the endothelial monolayer preparations from SHRSP
• The C(1)-C(10) bond cleavage and B ring aromatization of some 6-hydroxy-5.BETA.H-abieta-6,8,11,13-tetraen-18-oic acid 18,6-lactones.
• Functionalization of (R)-3-(3-acetoxypropyl)-2,3-dihydro-7-isopropyl-3,4-dimethylnaphtho(2,3-b)furan-2-one and some related compounds.
• Proliferative Property of the Microvessels of SHRSP Brains
• Effect of Antihypertensive Drugs on Acid Phosphatase Activity in Aorta in SHR:a preliminary report
• Aortic Proteases in Hypertensive Rats
• Synthetic Studies of the Flavone Derivatives. XVIII. The Syntheses of 5,7,3′-Trihydroxy-3,8,4′,5′-tetramethoxyflavone and Related Compounds
• The oxidation of some naphthols with benzoyl peroxide.
• Elastase and Collagenase Activities in The Aorta in SHRSP
• Synthetic Studies of the Flavone Derivatives. XXIII. The Synthesis of Eupatilin
• Synthetic Studies of the Flavone Derivatives. XXIV. The Synthesis of 5-Hydroxy-7,8,3′,4′-tetramethoxyflavone, A Pigment from Bergamott Oil
• The synthesis of methyl (15S)-16-hydroxydehydroabietate and its (15R)-epimer.
• Neuropsychological recovery in pediatric patients with acute subdural hematoma treated with mild hypothermia therapy : Report of two cases
• Effects of rat medial prefrontal cortex lesions on olfactory serial reversal and delayed alternation tasks
• The synthesis of ar-abietatrien-12,16-oxide and its C-15 epimer.
• Revision of structures of nellionol and dehydronellionol.
• The synthesis of (+)-premnolal.
• The total synthesis of (15R)- and (15S)-16-hydroxyferruginol.
• The synthesis of coleon B tri-O-methyl ether.
• Extraction of lanthanoids from hydrochloric and nitric acid solutions by di(2-ethylhexyl)phosphoric acid.
• The conversion of (+)-dehydroabietic acid into steroidal hormones.
• The total synthesis of (.+-.)-pisiferin.
• The Synthesis and Configuration of Fukiic Acid Derivatives
• Structure and synthesis of (+)-shonanol.
• Revision of structure of anhydronellionol triacetate.
• The Total Synthesis of (±)-Taxodione, A Tumor Inhibitor
• The Stereochemistry of Nucleophilic Addition. II. The Reformatsky Reaction of Methyl (+)-α-Bromopropionate, 2-Phenylpropanal, and 3-Phenyl-2-butanone
• The Stereochemistry of Nucleophilic Addition. V. The Reformatsky Reaction of 2-Phenylpropanal with Methyl α-Bromopropionate
• Synthetic Studies of the Flavone Derivatives. XXII. The Synthesis of Eupatoretin and Eupatin
• The Stereochemistry of Nucleophilic Addition. I. The Reformatsky Reaction of 2-Methyl- and 2-Ethylcyclohexanones
• The Stereochemistry of Nucleophilic Addition. IV. The Condensation of 2,2,6-Trimethylcyclohexanone with t-Butyl Acetate in the Presence of Lithium Amide
• Synthesis of taxodione, royleanone, cryptojaponol, and methyl 11-hydroxy-12-methoxy-7-oxoabieta-8,11,13-trien-18-oate.
• The syntheses and absolute configurations of nellionol and 5-dehydronellionol.
• Synthetic Studies of the Flavone Derivatives. XX. The Synthesis of Sorbifolin
• The reactions of .BETA.-amino enones with hydroxylamine.
• The regioselective amino-exchange reaction of .BETA.-amino conjugated enones.

もっと見る 閉じる

スポンサーリンク