Studies on the Syntheses of Heterocyclic Compounds. CCIX. Total Syntheses of (±)-Isococlaurine and (-)-Lotusine
スポンサーリンク
概要
- 論文の詳細を見る
Reductive dealkylation of 1-(4-benzyloxybenzyl)-3,4-dihydro-6,7-dimethoxyiso-quinoline (I) with lithium and liquid ammonia gave mainly isococlaurine (II) together with coclaurine (IV) as by-product, which were characterized as their tribenzoate, respectively. Furthermore, reductive methylation of II with formalin and sodium borohydride, followed by methylation with methyl iodide, afforded (±)-lotusine iodide (VII). Furthermore, synthesis and optical resolution of 6-acetoxy-1-(4-benzyloxybenzyl)-1,2,3,4-tetrahydro-2-methylisoquinoline (XII) was carried out to give our expected (+)-N-methylisococlaurine (VI), which was converted into the methiodide (VII), followed by treatment with sliver chloride, to give (-)-lotusine chloride (VIII). The total syntheses of (±)-isococlaurine and (±)-/(-) lotusine halides have been accomplished.
- 社団法人日本薬学会の論文
- 1968-01-25
著者
-
亀谷 哲治
Pharmaceutical Institute, Tohoku University School of Medicine
-
高野 誠一
Pharmaceutical Institute Tohoku University
-
佐々木 藤紀
Pharmaceutical Institute, Tohoku University School of Medicine
-
八巻 一彌
Pharmaceutical Institute, Tohoku University School of Medicine
-
八巻 一彌
東北大学医学部薬学科
-
亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
-
佐々木 藤紀
Pharmaceutical Institute Tohoku University School Of Medicine
関連論文
- Studies on the Syntheses of Heterocyclic Compounds. CXCV. The Structure of a Yellow Substance formed by Mild Oxidation of Aminopyrine.
- Synthetic Studies on β-Lactam Antibiotics. XIV. Synthesis of 7H-Azeto [1,2-a] thieno [2,3-c] pyridine Derivatives
- Total Syntheses of Didemnenones C and D
- EFFICIENT ENZYMATIC PREPARATION OF (+)- AND (-)-COREY LACTONE DERIVATIVES
- Synthetic Studies on Lythraceae Alkaloids via [3+2] Cycloaddition. I. Total Synthesis of Some Simple Phenylquinolizidine Alkaloids and Ester Alkaloids
- Syntheses of β-Carboline Derivatives. II. Pentacyclic β-Carboline Analogs of Alstoniline and Tetrahydrobenzindoloquinolizines.
- 2-(2-Pyridyl) indole Methiodide.
- Studies on the Synthesis of Heterocyclic Compounds. DXIX. A Total Synthesis of (±)-Discretine by Thermolysis
- A Novel Synthesis of Isopavine Ring System
- Studies on the Syntheses of Heterocyclic Compounds. DX. A Novel Rearrangement of proerythrinadienol with Methyl Fluorosulfonate
- Studies on the Syntheses of Heterocyclic Compounds. CDXCIII. Reaction of N-Ethoxycarbonyl-5-methoxytryptamine with Methyl Fluorosulfonate ("Magic Methyl")
- Novel Synthesis of Quinoline Derivatives with Triethyl Phosphite
- The Oxidation of p-Toluidine with Potassium Ferricyanide in Liquid Ammonia
- Benzyne Reaction. II. Syntheses of Benzyl Cyanide Derivatives by Benzyne Reaction (Studies on the Syntheses of Heterocyclic Compounds. CCXLVII)
- Studies on the Syntheses of Heterocyclic Compounds. CCXLV. The Mass Spectra of Cryptaustoline Type Alkaloids
- Studies on the Syntheses of Heterocyclic Compounds. CCXXXVIII. A Modified Synthesis of Pummerer's Ketone
- An Improved Synthesis of Styphnic Acid
- A Convenient Synthesis of 2-Cyclopentenone
- SELECTIVE FORMATION OF CHIRAL GLYCEROL ETHERS : A SYNTHESIS OF INTERMEDIATES OF A PLATELET-ACTIVATING FACTOR (C_-PAF)
- STEREOSELECTIVE SYNTHESIS OF (±)-SEMBURIN AND (±)-ISOSEMBURIN USING A COMMON BICYCLIC PRECURSOR
- ENANTIOSELECTIVE SYNTHESIS OF (-)-PHYSOSTIGMINE
- A New Prostaglandin Synthon from the 4-Oxatricyclo [4. 3. 0. 0^] non-8-ene System. A Total Synthesis of (±)-Prostaglandin F_
- Enantioselective Synthesis of the α-Pyrone Subunit of Verrucosidin
- Studies on the Syntheses of Tetracycline Derivatives. III. Synthetic Approach to Adriamycin-Synthesis of the Linear Tetracyclic Skeleton having the Same BC Ring System with Adriamycin
- An Alternative Synthesis of (±)-Dehydrogrisenfulvin by Enzymic Phenolic Oxidation by Homogenized Potato Peelings : Studies on the Syntheses of Heterocyclic Compounds. CCCLIII
- Electrolytic Oxidation. I. Phenolic Oxidation of p-Cresol by Electrolysis (Studies on the Syntheses of Heterocyclic Compounds. CCXXXVII
- Synthesis of Melanthioidine Derivative by Double Ullmann Reaction (Studies on the Syntheses of Heterocyclic Compounds. CCXXVI)
- Chichibabin Reaction. III. Chichibabin Reaction of 7-Methylquinoline and Migration of the Methyl Group in Friedel-Crafts Reaction of N-(m-Tolyl)- and N-(p-Tolyl)-β-chloropropionamide (Studies on the Syntheses of Heterocyclic Compounds. CCXV)
- Studies on the Syntheses of Heterocyclic Compounds. CCIX. Total Syntheses of (±)-Isococlaurine and (-)-Lotusine
- 1-置換-6,7-dimethoxy-3,4-dihydroisoquinoline誘導体の選択的脱メチル化ならびに(±)-Salsolineの改良全合成 : 複素環式化合物の合成研究 第165報
- The Nuclear Magnetic Resonance Spectra and Optical Rotatory Dispersion of Berbamunine, Magnoline and Two Diastereoisomers
- An Alternative Synthesis of Stereoisomeric Mixture of Magnoline by Ullmann Reaction (Studies on the Syntheses of Heterocyclic Compounds. CCXLVIII)
- Bisbenzylisoquinoline Alkaloids and Related Compounds. XI. Total Synthesis of Stereoisomeric Mixture of Magnoline
- Bisbenzylisoquinoline Alkaloids and Related Compounds. VI. A Modified Total Synthesis of the Stereoisomeric Mixture of Dauricine
- Capaurimine and Related Compounds. II. Syntheses of Position Isomers of Capaurimine and Capauridine : Studies on the Syntheses of Heterocyclic Compounds. CCCXIII
- An Alternative Synthesis of So-called Corpaverine (Studies on the Syntheses of Heterocyclic Compounds. CCXXXI)
- The Structure of Sendaverine and Its Total Synthesis
- Studies on the Syntheses of Heterocyclic Compounds. DCCLXVIII. Reaction of Pyrrolo [1,2-a] indole Derivatives with N-Bromosuccinimide in Protic Solvents
- Studies on the Syntheses of Heterocyclic Compounds. DCCLV. Iminoketene Cycloaddition. (4). Alternative Syntheses of 5,6,7,8-Tetrahydro-2,3-dimethoxy-8-oxoisoquinolo [1,2-b] quinazoline and Rutecarpine
- Studies on the Syntheses of Heterocyclic Compounds. DCCXXVIII. A Simple Synthesis of 1,3-Benzoxazin-4-ones from Salicylic Acid
- Studies on the Syntheses of Heterocyclic Compounds. DCXCII. A Novel Synthetic Route to Phthalideisoquinoline and Spirobenzylisoquinoline Type Alkaloids
- Studies on the Syntheses of Heterocyclic Compounds. DCXXVI. A Modified Synthesis of Pentazocine
- Studies on the Syntheses of Heterocyclic Compounds. CDLXXXVII. Photolytic Synthesis and Rearrangement of Proerythrinadienones
- Biotransformation of (+)-Reticuline in Rat
- Studies on the Syntheses of Heterocyclic Compounds. CDLII. An Alternative Total Synthesis of Corydalactam
- Studies on the Syntheses of Heterocyclic Compounds. CCCXXI. Synthesis of Isoquinoline Derivatives having Twenty-four Membered Ring System by Ullmann Reaction
- Studies on the Syntheses of Heterocyclic Compounds. DCXLI A Convenient Synthesis of Hexadehydroyohimbine and a Total Synthesis of Yohimbine
- Studies on the Syntheses of Tetracycline Derivatives. I. Thermolytic Cycloaddition of o-Quinodimethanes with Naphthoquinone
- Studies on the Syntheses of Heterocyclic Compounds. DXVI. Total Syntheses of the Aporphine, Morphinandienone, and Tetrahydrodibenzopyrrocoline Alkaloids by Benzyne Reaction
- Total Syntheses of (±)-N-Nordasycarpidone and (±)-Dasycarpidone (Studies on the Syntheses of Heterocyclic Compounds. CDXVIII)
- Studies on the Syntheses of Heterocyclic Compounds. DXXV. Syntheses of Berberine and Related Compounds. III. Dealkylation of N-Substituted Protoberberinium Salts
- イソヒノリン誘導体及び関連化合物の合成研究(第37報)Heterocyclic Acid Amide又はOximeに対するAllylbenzeneの反応による1-置換3-メチル-3,4-ジヒドロイソヒノリン誘導体の一新製法
- イソヒノリン誘導体及び関連化合物の合成研究(第36報)2'-(p-アミノフェニル)ピリミジノイソヒノリン誘導体の脱アミノ化
- イソヒノリン誘導体及び関連化合物の合成研究(第35報)ピリミジノイソヒノリン類の二重結合転移及び赤外吸収スペクトルによる推定構造
- Studies on the Syntheses of Heterocyclic Compounds. DCCCXCII. An Efficient Stereoselective Synthesis of Potential Intermediates for Rauwolfia Alkaloids from Furan and Its Derivatives
- Studies on the Syntheses of Heterocyclic Compounds. CDXXXIV. The Abnormal Formation of 3-(4-Methoxyphenethyl)-6,7-methylenedioxy-1,2,3-benzotriazin-4-one in Case of Pschorr Reaction
- Aztequine and Related Compounds. IV. A Synthesis of 2,2'-Dihydroxy-4,4'-bis (7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydro-1-isoquinolylmethyl) diphenyl Ether (Studies on the Syntheses of Heterocyclic Compounds. CCXXX)
- A Novel Dehydrazination Reaction. V. The Formation of Various Amides from Aliphatic and Aromatic Carboxylic Acid Hydrazides in the Presence of Chloral
- A Novel Dehydrazination Reaction
- Studies on the Syntheses of Heterocyclic Compounds. LXII. Synthesis of rac-Tetrahydrorotundine.
- Studies on the Syntheses of Heterocyclic Compounds. LIV. Formation of N-Alkyl-2-pyridone by Alkali Treatment of N-Alkyl-2-chloropyridinium Salt.
- Synthesis of rac-Tetrahydrorotundine
- Studies on the Syntheses of Heterocyclic Compounds. CDLVII. Synthesis of O-Benzylhomosalutaridine by Photolysis of Diazotized 1-(2-Aminophenethyl)-1,2,3,4-tetrahydroisoquinoline
- Modified Synthesis of Isosalutaridine (Studies on the Syntheses of Heterocyclic Compounds. CCCXXXVI)
- The Synthesis of C-nor-Androcymbine (Studies on the Syntheses of Heterocyclic Compounds. CCCXXIV)
- Formation of Morphinandienone-type Compound through Methylenedioxy Cleavage by Pschorr Cyclization
- Bisbenzylisoquinoline Alkaloids and Related Compounds. IX. A Modified Total Synthesis of Stereoisomeric Mixture of Magnolamine : Studies on the Syntheses of Heterocyclic Compounds. CXLV.
- Synthetic Approach to the Quassinoid Klaineanone : The Synthesis of a Potential Intermediate by Intramolecular Cycloaddition
- Synthesis of 1-Benzyloxindole Derivatives for the Study of Phenolic Oxidative Coupling (Studies on the Syntheses of Heterocyclic Compounds. CCCXLVII)
- Anti-cancer Agents. IV. : Desulfurization by Hydrazine Hydrate. (1). : The Reaction of o-, m-, and p-Nitrobenzyl Disulfide with Hydrazine Hydrate.
- Nitrenes. VIII. A Novel Synthesis of 3-Cyano-2-ethoxy-6,7-disubstitutedquinolines with Triethyl Phosphite (Studies on the Syntheses of Heterocyclic Compounds. CDXVI)
- Magnolamine and Related Compounds. N. An Alternative Synthesis of D (-) and L (+)-N-Methylcoclaurine.
- Bisbenzylisoquinoline Alkaloids and Related Compounds. VII. A Total Synthesis of the Stereoisomeric Mixture of Magnolamine
- Dienone Synthesis by Phenolic Oxidation of Dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline and Sodium Borohydride Reduction
- Bisbenzylisoquinoline Alkaloids and Related Compounds. Part XII. Synthesis of Stereoisomeric Mixture of Cuspidaline (Studies on the Syntheses of Heterocyclic Compounds. CCXXIX)
- Studies on the Syntheses of Heterocyclic Compounds. CCIV. Ring Contraction in the Catalytic Hydrogenation of 3-Oximino-4-oxoisocarbostyril.
- Studies on the Syntheses of Heterocyclic Compounds. DCLXXI. An Alternative Total Synthesis of Yohimbine
- Phenolic Cyclization. II. Syntheses of 6-Hydroxy-and 8-Hydroxy-1,2,3,4-tetrahydroisoquinoline Derivatives (Studies on the Syntheses of Heterocyclic Compounds. CCXXXII)
- Phenolic Cyclization. IX. Syntheses of Benz [c] phenanthridine and Related Compounds (Studies on the Syntheses of Heterocyclic Compounds. CDIX)
- Studies on the Syntheses of Heterocyclic Compounds. LIII. The Formation of Vanillide and Polyvanillide.
- Studies on the Syntheses of Heterocyclic Compounds. XLV. Synthesis of the Methyl Derivatives of Heterocyclic Compounds by the Hydrogenolysis of their Phenylurethans from Primary Alcohol.
- Studies on the Syntheses of Tetracycline Derivatives. II. Thermolytic Cycloaddition of o-Quinodimethanes with Tetrahydronaphthoquinone and Naphthoquinone
- Studies on the Syntheses of Analgesics. XLI. Optical Resolution of (±)-N-Cyclopropylmethyl-3-hydroxy-9-azamorphinan (Studies on the Syntheses of Heterocyclic Compounds. Part DCLXIX)
- Studies on the Syntheses of Analgesics. XLVI. An Abnormal Hofmann Degradation of N-(4-Hydroxybenzyl)-3-benzazocinium Halides (Studies on the Syntheses of Heterocyclic Compounds. DCLXVIII)
- Studies on the Syntheses of Analgesics. XXXIII. Synthesis of N-Methyl-N-[2-(3-methoxyphenyl)-2-phenyl] propylhydrazine (Studies on the Syntheses of Heterocyclic Compounds. CDXCVI.)
- Novel Methylation. Methylation of Tertiary Amines with Alkyl Salicylate
- Azamorphinan and Related Compounds. II. Synthesis of 3-Methoxy-9-azamorphinan Derivatives : Studies on the Syntheses of Heterocyclic Compounds. CCCXIX
- Azamorphinan and Related Compounds. I. A Synthesis of 3-Hydroxy-N-methyl-9-azamorphinan (Studies on the Syntheses of Heterocyclic Compounds. CCXIV)
- 複素環式化合物の合成研究(第151報) : 3,4-Dihydro-6,7,8-trimethoxyisoquinolineの選択的脱メチル反応ならびにAnhalamineの改良全合成
- Studies on the Syntheses of Heterocyclic Compounds. CLIX. The Reaction of 2-Nitro-1-indanone Oxime with Formalin and Hydrochloric Acid
- An Abnormal Formation of Indane from N-Phenethylphenylpropionamide under Bischler-Napieralski Reaction Conditions
- Studies on the Syntheses of Heterocyclic Compounds. DCCIX. A Synthetic Approach to Kesselringine
- Bisbenzylisoquinoline Alkaloids and Related Compounds. V. A Total Synthesis of Diastereoisomeric Mixture of Liensinine
- A New Selenium-Assisted Cyclization-A Biogenetic-type Synthesis of Safranal
- Synthetic Approach to the Grayanotoxins and Asebotoxins : A New Construction of A, B, and C Ring System of Grayanotoxan
- Studies on the Syntheses of Heterocyclic Compounds. DCCLIV. A Novel Method form Acetalisation of Formyl Group at the C_3-Position of 2,3-Dihydro-1H-pyrrolo [1,2-a] indole Skeleton
- Studies on the Syntheses of Heterocyclic Compounds. LII. The Eschweiler-Clarke and Pictet-Spengler Reactions with β-Methoxysafrylamine.
- Dienone-Phenol Rearrangement of"Procularine-type Compound"and Synthesis of Its Rearranged Cularine-type Compound. : Studies on the Syntheses of Heterocyclic Compounds. CCCVI
- Synthesis of Cularine Type Compounds (Studies on the Syntheses of Heterocyclic Compounds. CCXXXVI)
- Studies on the Syntheses of Heterocyclic Compounds. CLXXXII. A Modified Synthesis of So-called Corpaverine