57 麦角アルカロイド全合成研究

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概要

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• Various attempts were made to enlarge the scope of the common synthetic method for ergot alkaloids illustrated in Chart 1. I. The first total synthesis of (±)-chanoclavine-II (8) was achieved. Thus, epimerization at the C-4 position of the compound (7) afforded the corresponding 4,5-cis compound (10). A series of reactions according to the common synthetic method successfully converted 10 to 8. II. 2-Methoxymethyl-3-buten-2-ol, 2,5-trans-2-phenyl-5-vinyl-1,3-dioxan-5-ol, and optically active (R)-p-tolylvinylsulfoxide were examined as an olefin component in the second step of the common synthetic method. Cyclization of optically active 34 and 35 produced possible four optically active nitrosulfoxides (36; I, II, III, and IV) as shown in Table I. Major products, I and II, were established to be epimers at the C-4 configuration and therefore the reaction was found to proceed in 64% diastereoisomer excess. Establishment of absolute configurations of above stereoisomers is in progress. III. A new coupling reaction for unsymmetrical biaryls was elaborated and was designated as boronation-thallation method. It consists of the reaction of aryl thallium compounds with boronic acids in the presence of a catalytic amount of palladium salt and it tolerates to air and moisture. Applying this new reaction, direct introduction of aromatic and heteroaromatic compound into the 4-position of indole nucleus is realized. Photoreaction of 4-halogenoindoles was also proved to be a useful method for preparing 4-substituted indoles. A novel synthetic method for 4-(3-pyridyl)-3-indolecarbaldehyde (42) from 51 is also reported.

• 1986-09-09

著者

• 山田 文夫

  金沢大薬

• 染井 正徳

  金沢大・薬

• 山田 文夫

  金沢大・薬

• 甘利 裕邦

  金沢大・薬

• 大西 浩之

  金沢大・薬

• 巻田 吉彦

  金沢大・薬

• 大西 浩之

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 甘利 裕邦

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 巻田 吉彦

  Faculty Of Phermaceutical Sciences Kanazawa University

関連論文

• A TOTAL AND PRACTICAL SYNTHESIS OF ERGOT ALKALOID, (±)-AURANTIOCLAVINE
• 62 麦角アルカロイド、(±)-clavicipitic acidの5工程全合成(ポスター発表の部)
• 20 タリウムの化学を利用した新反応群の開拓とその天然物合成への応用(口頭発表の部)
• 52(PB1-1) 位置選択的なポリハロゲノインドール合成法とその天然物合成への応用(ポスター発表の部)
• TIN-THALL REACTION, A VERSATILE METHOD FOR CROSS COUPLING TIN COMPOUNDS WITH THALLIUM COMPOUNDS(Communication to the Editor)
• BORONATION-THALLATION, A NEW APPROACH TO THE SYNTHESIS OF INDOLES HAVING ARYL AND/OR A HETEROARYL SUBSTITUENT AT THE 4-POSITION
• 57 麦角アルカロイド全合成研究
• SHORT-STEP SYNTHESIS OF THE ERGOT ALKALOIDS, (±)-NORCHANOCLAVINE-I, (±)-CHANOCLAVINE-I, (±)-ISOCHANOCLAVINE-I, AND (±)-AGROCLAVINE
• The Chemistry of Indoles. XXVII. : A Practical Synthesis of the 1-Methoxy Analog of an Ergot Alkaloid, (±)-1-Methoxy-6,7-secoagroclavine
• TOTAL SYNTHESIS OF (±)-PANICULIDINE B
• The Chemistry of Indoles. XXIV. Syntheses of 3-Indoleacetic Acid and 3-Indoleacetonitrile Having a Halogeno Group and a Carbon Functional Group at the 4-Position
• 29 短工程かつ実用的な麦角アルカロイド全合成
• A PRACTICAL SYNTHESIS OF THE ERGOT ALKALOID (±)-6,7-SECOAGROCLAVINE
• The Chemistry of Indoles. XIII. Syntheses of Substituted Indoles carrying an Amino, Nitro, Methoxycarbonyl, or Benzyloxy Group at the 4-Position and Their 1-Hydroxy Derivatives
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