Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines

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概要

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• Chiral syntheses of 3-methyl-5-(phenylthio)-L-histidine (8a) and 3-methyl-5-(1-naphthalenylthio)-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have been accomplished through a 10-step route starting from 4(5)-bromoimidazole (9). The key steps involved were methylation of 9, hydroxymethylation of 4-bromo-1-methyl-1H-imidazole (11), replacement of the 4-bromo group by an arylthio group in the aldehyde 14, and introduction of a chiral α-amino acid moiety into the chlorides 17a and 17b by the 'bis-lactim ether' method. The synthesis of the 4-(4-methoxybenzyl)thio analogue 17c, carried out in a similar manner, concluded formal syntheses of ovothiols A and C (1 and 3).

• 公益社団法人日本薬学会の論文
• 1994-09-15

著者

• 藤井 澄三

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  金沢大学薬学部

• 大場 正志

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 大場 正志

  Kanazawa Univ. Ishikawa Jpn

• Ohba M

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 向平 貴文

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

• 向平 貴文

  Faculty Of Pharmaceutical Sciences Kanazawa University

関連論文

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• Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
• Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
• Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
• Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
• Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
• Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
• Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
• Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
• Lactams. VII. Stereochemical Characterization and Cis-Trans Isomerization of 5-Ethyl-2-oxo-4-piperidineacetic Acid and Related Compounds
• Lactams. XVII. Synthesis and Stereochemical Characterization of Diethyl cis-and trans-5-Ethyl-2-oxo-4-piperidinemalonate
• Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
• Purines. XLI. : An Alternative Synthesis and the Chemical Behavior of 7,9-Dialkyladeninium Salts
• Purines. XXXVIII. A General Synthesis of 7,9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N^6-Alkoxy Group as a Control Synthon
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• Lactams. VI. Synthesis and Nuclear Magnetic Resonance Study of 1-Aralkyl-3-methyl- and -5-methyl-2(1H)-pyridones
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• Purines. LXII. Both Enantiomers of N^6-(1,3-Dimetyl-2-butenyl)adenine and Their 9-β-D-Ribofuranosides : Synthesis and Cytokinin Activity
• Purines. LV. Syntheses and cytokinin activities of some adenine and adenosine derivatives related to 1'-methylzeatin
• Pourines. XLV. : Syntheses and Cytokinin Activities of the Cis Isomers of (1'R)-1'-Methylzeatin and Its 9-β-D-Ribofuranoside
• Purines. XXXV. : Synthesis and Cytokinin Activity of Racemic 1'-Methylzeatin
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• フリニルアミノ酸,フリニルヘフタイトおよび関連化合物のサイトカイニン活性について(A. 理学)
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• Purines. LIV. Intramolecular Cyclization of 9-Ethyl-1-(2-hydroxyethyl)adenine Caused by Nucleophiles : Formation of N^6,1-Ethanoadenine Derivatives
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• Purines. XV. Conversion of N, 9-Dimethyladenine into the 1,9-Dimethyl Isomer : A Reverse Operation of the Dimroth Rearrangement
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• Lactams. XVIII. Oxidation of 1-Substituted 3-tert-Butyl-piperidine with Mercuric Acetate-EDTA
• Lactams. XIX. The Alkaline Ferricyanide Oxidation of 1,3-Disubstituted Pyridinium Salts : Effects of Branched Alkyl Groups at the 3-Position
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• The Preparation of 3,4-Dimethoxy-and 3,4-Methylenedioxy-Phenethyl Alcohol
• Purines. XXXVI. : Fission and Reclosure of the Adenine Ring in 3,9-Disubstituted Adenines : Effects of Substituents
• Purines. XXXIV. : 3-Methyladenosine and 3-Methyl-2'-deoxyadenosine : Their Synthesis, Glycosidic Hydrolysis, and Ring Fission
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• Preparation of Some Ring-Oxygenated Phenacyl Bromides
• Lactams. XIV. cis-trans Isomerization in the 5-Ethyl-2-oxo-4-piperidineacetic Acid System under Fischer-Speier Esterification Conditions
• Lactams. XII. Improvements in the Synthesis of Ethyl trans-5-Ethyl-2-oxo-4-piperidineacetate
• Lactams. XI. Construction of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Carbonyl and Related Groups at the 3-Position
• Lactams. IX. Generation of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Hydrocarbon Substituents at the 3-Position

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