Chemical Transformation of (+)-Dehydroabietic Acid Leading to a Formal Synthesis of (+)-Coleon A
スポンサーリンク
概要
- 論文の詳細を見る
(R)-6-Hydroxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho[2,3-b]furan-2(3H)-one (3), prepared from (+)-dehydroabietic acid (2), was converted into (R)-9-acetoxy-6-benzoyloxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho[2,3-b]furan-2,5,8(3H)-trione (10) and its 9-acetyl compound (11) by a series of reactions : sodium borohydride reduction, acetylation, alkaline hydrolysis, benzoyl peroxide oxidation, Jones oxidation, and m-chloroperbenzoic acid oxidation. The trione 10 was further transformed into (R)-5,6,8,9-tetraacetoxy-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho[2,3-b]furan-2(3H)-one (15) by alkaline hydrolysis and reductive acetylation. Since the conversion of 15 into coleon A (1) has already been reported, the present work can be regarded as a new formal synthesis of coleon A.
- 公益社団法人日本薬学会の論文
- 1991-11-25
著者
-
松本 高志
Faculty Of Integrated Arts And Sciences The University Of Tokushima
-
寺尾 博充
徳島大総合科
-
今井 幸彦
Suzugamine Women's College
-
松本 高志
Department of Applied Material Science, Faculty of Integrated Arts and Science University of Tokushi
-
寺尾 博充
Department of Applied Material Science, Faculty of Integrated Arts and Science University of Tokushi
-
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
-
Matsumoto Takashi
Faculty Of Integrated Arts And Sciences The University Of Tokushima
関連論文
- Lipase-Catalyzed Hydrolysis of Some Racemic 1-Acetoxy-2-arylpropanes
- 17aWE-7 テトラブロモアンチモン(III)酸4-アミノピリジニウムのNQR、NMR
- Rabdokaurins C and D, Two New Diterpenes from Rabdosia longituba
- Total Synthesis of (±)-Porosin, a Neolignan from Ocotea porosa and Urbanodendron verrucosum (Lauraceae)
- 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
- Lipase-Catalyzed Resolution of Racemic 1-Acyloxy-2-(p-tolyl)propanes
- 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
- 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
- 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
- 13aTL-6 テトラブロモビスマス (III) 酸 4-アミノピリジニウムの NQR(誘電体, 領域 10)
- 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.