Total Synthesis of (±)-Porosin, a Neolignan from Ocotea porosa and Urbanodendron verrucosum (Lauraceae)

スポンサーリンク

概要

• 論文の詳細を見る

• Veratraldehyde was condensed with methyl 2-chloropropanoate to give a glycidic ester. This was hydrolyzed with aqueous sodium hydroxide and the resulting sodium salt was treated with lead(IV) tetraacetate to give 1-acetoxy-1-(3,4-dimethoxyphenyl)propan-2-one (13). Condensation of 13 with dimethyl malonate, followed by acidic hydrolysis and sodium borohydride reduction afforded (2R^*, 3S^*, 4R^*)-4-(3,4-dimethoxyphenyl)-2-methoxycarbonyl-3-methyl-4-butanolide (7a). The γ-lactone 7a was then converted into 5'-demethoxyporosin (10) by means of a series of reactions : Michael reaction with methyl vinyl ketone, elimination of the methoxycarbonyl group, acetalization, allylation, deacetalization, and intramolecular aldol reaction. Introduction of a hydroxyl group at the C-5' position in 10,followed by methylation with diazomethane afforded racemic porosin. The synthetic porosin was further converted into 5-demethoxymegaphone acetate.

• 社団法人日本薬学会の論文
• 1995-12-15

著者

• 松本 高志

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• 武田 美雄

  徳島大学総合科学部生物環境資源化学分野

• 武田 美雄

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• 武田 美雄

  Faculty Of Pharmaceutical Sciences The University Of Tokushima

• Fujii K

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• 藤井 和慈

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• 大岩本 雅紀

  Faculty of Integrated Arts and Sciences, The University of Tokushima

• 岸田 正志

  Faculty of Integrated Arts and Sciences, The University of Tokushima

• 渋谷 博

  Faculty of Integrated Arts and Sciences, The University of Tokushima

• 今井 幸彦

  Suzugamine Women's College

• 渋谷 博

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• Takeda Yoshio

  Faculty Of Integrated Arts And Science The University Of Tokushima

• Imai S

  Niigata Univ. Pharmacy And Applied Life Sci. Niigata Jpn

• 今井 幸彦

  Suzugamine Women's College

• Imai Sachihiko

  Suzugamine Women's College

• 岸田 正志

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• 大岩本 雅紀

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

• Matsumoto Takashi

  Faculty Of Integrated Arts And Sciences The University Of Tokushima

関連論文

• 2 アジサイ(Hydrangea)属植物の新型セコイリドイド配糖体について
• ステビア中の抗酸化性物質の同定
• Lipase-Catalyzed Hydrolysis of Some Racemic 1-Acetoxy-2-arylpropanes
• Studies on Monoterpene Glucosides and Related Natural Products. XXIII. Biosynthesis of the Secoiridoid Glucosides, Gentiopicroside, Morroniside, Oleuropein, and Jasminin
• Studies on Monoterpene Glucosides and Related Natural Products. XVIII. Formation Sequences of Iridoid Glucosides in highly Oxidized Levels
• Studies on Monoterpene Glucosides and Related Natural Products. XVII. The Intermediacy of 7-Desoxyloganic Acid and Loganin in the Biosynthesis of Several Iridoid Glucosides
• Studies on Monoterpene Glucosides and Related Natural Products. XIII. Incorporation of [10-^C]-Sweroside into Gentiopicroside and the Alkaloids in Vinca and Cincona Plants
• Biopharmaceutical Studies of Thiazide Diuretics. I. Determination of pK_a Values and Partition Coefficients of Thiazide Diuretics
• On the Diterpenoids of Andrographis paniculata : X-Ray Crystallographic Analysis of Andrographolide and Structure Determination of New Minor Diterpenoids
• チョロギStachys sieboldi MIQ.の配糖体成分とそのヒアルロニダーゼ活性に及ぼす影響
• コラーゲン線維形成抑制成分の探索
• Studies on the Constituents of Solanum Plants. V. The Constituents of S. lyratum THUNB. II
• Revision of the Structures of Isodonal, Rabdolasional and Related Diterpenoids
• Studies on the Diterpenoid Constituents of Rabdosia ternifolia : Structural Elucidation of New Diterpenoids, Rabdoternins A, B and C
• Rabdosia ternifolia(D.DON)HARAの成分 : 新ジテルペンIsodonoic Acidの構造
• 36 中国産Rabdosia属植物R.phyllostachys,R.rubescensならびにR.sculponeataの新ジテルペンの構造
• Studies on the Blue Pigments Produced from Genipin and Methylamine. II .On the Formation Mechanisms of Brownish-Red Intermediates Leading to the Blue Pigment Formation
• Studies on the Blue Pigments Produced from Genipin and Methylamine. I. Structures of the Brownish-Red Pigments, Intermediates Leading to the Blue Pigments
• 75 Genipinとアミノ酸より生成するPseudoazulene骨格をもつ青色々素の構造に関する研究
• Studies on Monoterpene Glucosides and Related Natural Products. XXXIX. Biogenetic-type Transformation of Geniposide into Plumieride
• モノテルペン配糖体及び関連物質に関する研究(第65報)Amarogentin及びAmaroswerinのBiphenylcarboxylic Acid部分の生合成
• Rabdokaurins C and D, Two New Diterpenes from Rabdosia longituba
• Marrubinones A and B, New Labdane Diterpenoids from Marrubium astracanicum (Labiatae)
• Fungal Metabolites. XV. Primary Structures of Antibiotic Peptides, Hypelcins B-I, B-II, B-III, B-IV and B-V, from Hypocrea peltata. Application of Electrospray Mass Spectrometry and Electrospray Mass Spectrometry/Mass Spectrometry
• Studies on Monoterpene Glucosides and Related Natural Products. XXXIV. Two Further New Glucosides from the Fruit of Gardenia jasminoides ELLIS forma grandiflora (LOUR.) MAKINO
• Studies on Monoterpene Glucosides and Related Natural Products. XXXII. Iridoid Glucosides of Tarenna kotoensis var. gyokushinka
• モノテルペン配糖体および関連天然物の研究(第25報)クチナシGardenia jasminoides ELLIS forma grandiflora [LOUR.]MAKINOのイリドイド配糖体について その1
• クロキSymplocos lucidaのLignan配糖体について
• 沖縄産食薬用植物エタノール抽出物の抗酸化関連活性
• 同科同属の植物種による含有成分の違いと、アキチョウジにみられる同種間の含有成分の多様性 (特集 天然物の基原と品質)
• Total Synthesis of (±)-Porosin, a Neolignan from Ocotea porosa and Urbanodendron verrucosum (Lauraceae)
• Alangionosides G-M : Glycosides of Megastigmane Derivatives from the Leaves of Alangium premnifolium
• Enantioselective Biotransformation of 1-Isopropylnaphthalene in Rabbits
• The Enantioselective Metabolism of 4-Isopropenyltoluene in Rabbits
• (+)-デヒドロアビエチン酸のデス-Aステロイドへの変換
• Rearrangement of the Angular Methyl Group in Dehydroabietic Acid Derivatives
• Absolute Structure of Ionol Glucoside : A Single-Crystal X-Ray Analysis of Dendranthemoside A Pentaacetate
• Lipase-Catalyzed Resolution of Racemic 1-Acyloxy-2-(p-tolyl)propanes
• Conformation and Absolute Sterochemistry of Macrocalyxoformin D (=Longirabdiol)
• The Enantioselective Metabolism of p-Cymene in Rabbits
• センリョウ果実のフェノール性化合物の単離と同定
• (15S)-12,16-ジヒドロキシ-8,11,13-アビエタトリエン-18-カルボン酸メチルエステルとそれの(15R)-エピマーの過酸化ベンゾイル酸化
• Inorganic Chemical Approaches to Pharmacognosy. VII. : X-Ray Fluorescence Spectrometric Studies on the Inorganic Constituents of Crude Drugs. (5). The Relationship between Inorganic Constituents of Plants and the Soils on Which They Are Grown
• Isolation and Characterization of New Diacyl 6-O-α-L-Rhamnopyranosylcatalpols from the Leaves of Premna japonica MIQ.
• Diterpenoid Constituents of Rabdosia umbrosa (MAXIM.) : Isolation and Structure Elucidation of Two New Diterpenoids, Umbrosianin and Rabdoumbrosanin
• Studies on the Diterpenoids of Rabdosia longituba (MIQ.) HARA : Structure of a New Bitter Diterpenoid, Rabdolongin A, and the Absolute Stereochemistry of Rabdolongin B (=Maoecrystal D)
• An Intramolecular Hydride Shift in Derivatives of Kamebakaurin and kamebacetal A
• Fungal Metabolites. II. Structural Elucidation of Minor Metabolites, Valinotricin, Cyclonerodiol Oxide, and Epicyclonerodiol Oxide, from Trichoderma polysporum
• FURTHER INVESTIGATION OF PEPTIDE ANTIBIOTIC, HYPELCIN A : ISOLATION AND STRUCTURES OF HYPELCINS A-I, A-II, A-III, AND A-IV
• A New Synthesis of 3-Oxosapriparaquinone, a Diterpene from Salvia prionitis HANCE (Libiatae)
• Synthesis of Pygmaeocine E, a Linear Abietane Diterpene from Pygmaeopremna herbacea (ROXB.) MOLDENKE
• Synthesis of 6-Methoxy-1,1,10-trimethyl-1,2,3,4-tetrahydroanthracene, a Synthetic Intermediate of a Linear Abietane Diterpene, Umbrosone
• Skeletal Rearrangement of the Dehydroabietic Acid Derivative
• Studies on Monoterpene Glucosides and Related Natural Products. XLII. On the Possibility of the Intermediacy of 10-Hydroxyloganin in the Biosynthesis of Secologanin
• Studies on Monoterpene Glucosides and Related Natural Products. XLI. Chemical Conversion of Geniposide into 10-Hydroxyloganin
• 103 Neoantimycinの生合成-立体化学的側面(ポスター発表の部)
• Chemical Transformation of (+)-Dehydroabietic Acid Leading to a Formal Synthesis of (+)-Coleon A
• ステロイド骨格のB,CおよびD環をもつ三環性ステロイド類縁体の合成
• Revised Structures of Inflexin and Related Diterpenoids
• NEW SECOIRIDOID GLUCOSIDES, HYDRANGENOSIDES E, F AND G FROM HYDRANGEA SCANDENS
• Novel Type Secoiridoid Glucosides, Hydrangenosides B, C and D from Hydrangea macrophylla
• Studies on the Bacterial Gall of Myrica rubra : Isolation of a New [7,0]-Metacyclophan from the Gall and DL-β-Phenyllactic Acid from the Culture of Gall-Forming Bacteria(Pharmacognosy,Chemical)
• 4 カメバヒキオコシの新ジテルペン,Leukamenin類の構造
• Studies on Monoterpene Glucosides and Related Natural Products. XXX. The Fate of the C-8 Proton of 7-Deoxyloganic Acid in the Biosynthesis of Secoiridoid Glucosides
• 植物染料hennaの配糖体と品質について
• The Synthesis of Hyptol and Its C-15 Epimer from (+)-Dehydroabietic Acid.
• Conversion of (+)-8,11,13-Abietatriene into (15R)-16-Hydroxyferruginol and Its (15S)-Epimer.
• P-12 抗酸化性フェノール酸類の脂質抗酸化反応生成物の単離と構造(ポスター発表の部)

もっと見る 閉じる

スポンサーリンク