Synthetic Studies on Isoquinoline Alkaloids. I. An Efficient Synthesis of 9,10-Substituted Protoberberine Alkaloids

スポンサーリンク

概要

• 論文の詳細を見る

• Three synthetic routes leading to the 9,10-disubstituted tetrahydroprotoberberine derivative (4a) were investigated. The third route involving a four-step reaction sequence starting from homoisovanillinic acid (13b) afforded 3-benzyloxy-9,10-dimethoxy-tetrahydroprotoberberine (4a) in 65% over-all yield providing the most efficient and general synthesis of the hitherto not easily available 9,10-disubstituted protoberberine alkaloids. The key step in this synthesis was effective conversion of 13b into the 7,8-disubstituted isochromanone derivative (28b) which required specific introduction of hydroxymethyl into the position ortho to the phenolic function in 13b. This was nicely effected our newly discovered general method for ortho-(α-hydroxy)-alkylation of phenols using benzeneboronic acid.

• 社団法人日本薬学会の論文
• 1975-11-25

著者

• 永田 亘

  塩野義製薬株式会社研究所

• 岡田 京

  Shionogi Research Laboratory

• 若林 利生

  Shionogi Research Laboratory

• 徳竹 伯夫

  Patent Department

• 若林 利生

  Shionogi Research Laboratory:(present Address)central Research Institute Teijin Limited

• 徳竹 伯夫

  Shionogi Research Laboratory Shionogi & Co. Ltd.

• 板崎 弘

  Shionogi Research Laboratories Shionogi & Co. Ltd.

関連論文

• Synthesis of 17-Hydroxyimino Steroids and their O-Alkyl Derivatives
• Thiosteroids. XXXVI. Synthesis of Some 16-Sulfur-substituted Steroids
• Bile Acids and Steroids. XXXII. Thiosteroids. (17). Synthesis of 16β-Acetylthio-and 16β-Alkylthio-estratriene Derivatives
• Bile Acids and Steroids. XXV. Thiosteroids. (10). Synthesis of Some 16β-Acetylthio- and 16β-Alkylthio-estrones and their Derivatives
• 6. dl-ジベレリンA_の生理活性
• オキサセフェム系抗生物質の開発研究
• Studies of Antitumor-Active 5-Fluorouracil Derivatives. I. Synthesis of N-Phthalidyl 5-Fluorouracil Derivatives
• 1-オキサセフェム誘導体の合成と抗菌活性 (「医薬品開発をめぐる生理活性物質の合成」特集号)
• 63 分子内閉環による7α-メトキシ-1-オキサセフェム骨格の新しい立体制御的合成
• 新しい骨核を有する合成β-ラクタム抗生物質 (新しい抗生物質の開発と合成)
• Synthetic Studies on Isoquinoline Alkaloids. I. An Efficient Synthesis of 9,10-Substituted Protoberberine Alkaloids
• Synthesis of Bridged Steroids. VII. B-Norsteroids having a Gibbane B-C-D Ring System. (2). Synthesis of the 7-Deoxygibberellin Type Ring System
• Synthesis of Bridged Steroids. VI. B-Norsteroids having a Gibbane B-C-D Ring System. (1). Synthesis of 5-Cyano-B-norsteroids via Hydrocyanation
• 39 dl-ジベレリンA_の立体選択的全合成に於る問題点
• 37 C_ジベレリン類の全合成的研究
• Synthesis of Bridged Steroids. III. Cholestane Derivatives having a Bridged Bicyclo [2. 2. 2] octane Ring System of the Atisine Type
• Synthesis of Bridged Steroids. II. Steroids having a Bridged Bicyclo [3. 2. 1] octane Ring System of the Kaurene Type
• Synthesis of Bridged Steroids. I. Steroids having a Bridged Bicyclo [3. 2. 1] octane Ring System of the Phyllocladene Type
• Nuclear Magnetic Resonance Spectroscopic Evidence for Distorted Conformations of the C-Rings in 8β, 11β- and 11β, 13β-Bridged Steroids
• 28.新hydrocyanation法とそのステロイド合成への応用
• 医薬化学部会の設立について
• Synthesis of 2,3-Dihydro-1,4-benzodioxin Derivatives. II. : 5(or 6)-Acyl 2,3-Dihydro-1,4-benzodioxin Derivatives : New Phenoxyacetic Acid Diuretics
• Synthesis of 2,3-Dihydro-1,4-benzodioxin Derivatives. I. : 2-Substituted-5(and 6)-sulfamoyl-2,3-dihydro-1,4-benzodioxins
• 有機合成化学 : その現代的意義
• 5α-Pregnan-3β-ol-20-one及びLatifoline,Conessineの全合成
• 1-オキサセフェム誘導体の合成と抗菌活性
• Synthetic Studies on Isoquinoline Alkaloids. II. Selective Conversion of 3,9,10-Substituted Tetrahydroprotoberberines into 3,9,10-Substituted 14-Deoxoprotopines. Total Synthesis of 3,9,10-Substituted 5,6,7,8,13,14-Hexahydrodibenz (c, g) azecines

もっと見る 閉じる

スポンサーリンク