Utilization of Protopine and Related Alkaloids. VI. Transformation of Berberine to 10b-Methylhexahydrobenzo [c] phenanthridine Derivative

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概要

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• The methine base (X) derived from berberine chloride via several steps is photocyclized to the two isomeric carbinolamine forms (XI and XII) of 10b-methyl-4b, 10b, 11,12-tetrahydrochelerythrine. Spectral data and chemical evidences reveal that the positions of the hydroxyl groups are C-6 in XI and C-4b in XII. The cis B/C ring juncture in XI is determined by observation of the nuclear Overhauser effect between 10b-Me and 4b-H. The formation pathways of XI and XII are examined and deduced to be the photoinduced intramolecular alkylation on carbon in the enamine system with olefin.

• 社団法人日本薬学会の論文
• 1973-06-25

著者

• 阿部 薫

  School Of Pharmaceutical Sciences Kitasato University

• 恩田 政行

  School of Pharmaceutical Sciences, Kitasato University

• 湯浅 久美子

  School of Pharmaceutical Sciences, Kitasato University

• 岡田 順子

  School of Pharmaceutical Sciences, Kitasato University

• 片岡 京子

  School of Pharmaceutical Sciences, Kitasato University

• 片岡 京子

  School Of Pharmaceutical Sciences Kitasato University

• 岡田 順子

  School Of Pharmaceutical Sciences Kitasato University

• 湯浅 久美子

  School Of Pharmaceutical Sciences Kitasato University

関連論文

• Utilization of Protopine and Related Alkaloids. VI. Transformation of Berberine to 10b-Methylhexahydrobenzo [c] phenanthridine Derivative
• Utilization of Protopine and Related Alkaloids. V. The Adduct of Photoproduct of Anhydromethylberberine with Dimethyl Acetylenedicarboxylate
• Utilization of Protopine and Related Alkaloids. IV. Transformation of Protopine and Protoberberine Alkaloid to Benzo [c] phenan-thridine Alkaloid
• Studies on Morphine Alkaloids. VII. Microbial Transformation of 14β-Bromocodeinone
• Studies on the Constituents of Bocconia cordata. II. Bocconine
• Utilization of Protopine and Related Alkaloids. III. Acid Catalyzed Cyclization of Anhydromethylberberine. The Revised Structures for Hydroxyisoanhydrodihydromethyl-berberine and Isoanhydromethylberberine
• Studies on Morphine Alkaloids. VI. Indolinocodeine. IV. Conversion of Indolinocodeine Series Compounds into Morphine Series Compounds
• Studies on Morphine Alkaloids. V. Reaction Mechanism of the Reduction of 14β-Bromocodeinone with Sodium Borohydride
• Transformation of Protopine to Sanguinarine. Photocyclization of Anhydroprotopine
• On the Double Bond Nature (endo or exo) in the Condensation Products of Cyclic Ketones with Cyanoacetate or Cyanoacetic Acid
• Utilization of Protopine and Related Alkaloids. I. Ring Closure of Anhydroprotopine
• Studies on Morphine Alkaloids. IV. Indolinocodeine. III. Preparation of 9α-Substituted Indolinocodeine
• Studies on Morphine Alkaloids. III. Indolinocodeine. II. 9α-Methoxyindolinocodeine
• Utilization of Protopine and Related Alkaloids. XVI. Nuclear Magnetic Resonance Spectroscopy on the Cycloadducts of Anhydromethylberberines with Dienophiles
• Heterocycles. XXII. : Stereoselective Synthesis of (+)-Aromadendrin Trimethyl Ether and Its Enantiomer, and Their Reduction
• Heterocycles. XX. : Reactions of 2"-Methoxymethoxychalcone Epoxides under Acidic Conditions
• Utilization of Protopine and Related Alkaloids. XVII. Spectroscopic Studies on the Ten-Membered Ring Conformations of Protopine and α-Allocryptopine
• Heterocycles. XVII. Sodium Borohydride Reduction of Flavanonols and Hydrolysis of (±)-Fistacacidin Acetates
• Structure Elucidation of Pantherine, a Flycidal Alkaloid from Amanita pantherina (DC.) FR.
• Heterocycles. XV. Enantioselective Synthesis of Chiral Flavanonols and Flavan-3,4-diols
• The Alkaloid AM-6201 from Streptomyces xanthochromogenus
• Oxaline and Neoxaline
• Alkaloid from Thermoactinomyces Species
• Revised Structure for an Alkaloid from Streptomyces sp. NA-337
• Utilization of Protopine and Related Alkaloids. XV. Photolysis of 4-Methyl-1-oxoanhydroberberine
• Utilization of Protopine and Related Alkaloids. XIV. Oxidation of the Photoadduct of 1-Oxoanhydromethylberberine with Nitrosobenzene, and Synthesis of Ring C-Substituted Benzo [c] phenanthridines
• Heterocycles. XIII. Syntheses and Absolute Configurations of Chiral Benzo [c] phenanthridines
• Utilization of Protopine and Related Alkaloids. XIII. Attempts to obtain Useful Intermediates for the Syntheses of Chelidonine and Homochelidonine
• Heterocycles. XI. Syntheses of Analogs of 10b-Hydroxychelidonine and 4b-Epichelidonine
• Heterocycles. X. Syntheses and Absolute Configurations of a Chiral Naphthoquinone Epoxide and Chiral Naphtho [1,2-c] isocoumarins
• Heterocycles. VIII. Syntheses of 12-Acetoxybenzo [c] phenanthridines
• Utilization of Protopine and Related Alkaloids. XII. An Improved Route to an Analog of the Alkaloid Corynoline
• Utilization of Protopine and Related Alkaloids. XI. Photolysis of 7,8-Dimethoxy-2-methyl-3-(4', 5'-methylenedioxy-2'-vinyl-phenyl) isocarbostyril and Its Application to the Preparation of Oxychelerythrines
• Formation of 6-Acetoximino-3β-acetoxycholestan-5α-ol Nitrite and Its Reduction over Adams'Platinum
• Products from Reaction of Cholesteryl Acetate with Nitrous Acid
• Steroids. VII. Photolysis of 3β, 5α-Diacetoxy-6-nitriminocholestane
• Steroids. VI. Alumina-Induced Reaction of 3β, 5α-Diacetoxy-6-nitriminocholestane
• Steroids. V. Photolyses of Steroidal Oxime Acetates
• Steroids. III. Alumina-Induced Reactions of Steroidal Oxime Acetates
• Diterpenoids. XXXVIII. Conversion of l-Abietic Acid into Steroidal Skeletons : Formation of the D-Ring (1)
• Isoquinolines. I. Preparation and Stereochemistry of 9,10-Epoxy-1-(p-methoxybenzyl)-2-methyldecahydroisoquinolines
• Synthesis of the Alkaloid from Thermoactinomyces Species
• Steroids. IV. Revised Structure for the Product from 3β-Acetoxycholest-5-ene with Nitrous Acid
• Heterocycles. VII. Reaction of 12-Hydroxy-5-oxa-6-oxo-5,6-dihydrochrysene with Methylamine
• Heterocycles. VI. An Approach to Corynoline Analogues
• Heterocycles. IV. Photolyses of the 4-Arylacetylated 1,2-Dihydroisoquinoline, Isocarbostyril and Its Enol Acetates
• Conversion of Dehydroabietic Acid into a Steroid Skeleton : Formation of the D-Ring. II
• Conversion of Dehydroabietic Acid into a Steroid Skeleton : Formation of the A-ring. III.
• Conversion of Dehydroabietic Acid into a Steroid Skeleton : Formation of the A-Ring. II
• Conversion of Dehydroabietic Acid into a Steroid Skeleton : Formation of the A-Ring. I
• Study on Synthesis of Antipodal Steroid
• Heterocycles. III. Syntheses of Berbans from 6,7-Dimethoxy-3,4-dihydroisoquinoline
• Utilization of Protopine and Related Alkaloids. IX. Formation of 4b, 6-Epidioxybenzo [c] phenanthridine Derivative and Its Reaction with 2,3-Dichloro-5,6-dicyanobenzoquinone
• Utilization of Protopine and Related Alkaloids. VIII. Synthesis of an Analogue of Alkaloid Corynoline

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