Highly Stereoselective Total Synthesis of Methynolide, the Aglycon of the 12-Membered Macrolide Antibiotic Methymycin. I. Synthesis of a Prelog-Djerassi Lactone-Type Chiral Intermediate from D-Glucose(Organic,Chemical)

スポンサーリンク

概要

• 論文の詳細を見る

• For the highly stereoselective synthesis of methynolide (2), the aglycon of the 12-membered macrolide antibiotic methymycin (1), a Prelog-Djerassi lactone-type chiral intermediate (7a) bearing four chiral centers corresponding to the C-2, C-3, C-4, and C-6 positions was synthesized from D-glucose. In this synthesis, several stereocontrolled reactions such as hydroboration, catalytic hydrogenation, etc. were successfully applied. The utility of the 4-methoxybenzyl protecting group was also demonstrated.

• 社団法人日本薬学会の論文
• 1987-06-25

著者

• 及川 裕二

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 及川 裕二

  北大薬

• 田中 達義

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 堀田 清

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 野田 一生

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 堀田 清

  Faculty Of Pharmaceutical Sciences Health Science University Of Hokkaido

• 田中 達義

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 野田 一生

  Faculty Of Pharmaceutical Sciences Hokkaido University

関連論文

• An Application of Reactions of β-Ketosulfoxides to Estrone Synthesis
• 33 ケトスルホキサイドを利用した合成研究 : Olivacine,Ellipticine,Estroneの合成
• A Stereoselective Total Synthesis of (9S)-9-Dihydroerythronolide A via Coupling between the Right-Half (C1-C6) Aldehyde and the Left-Half (C7-C15) Sulfoxide
• Synthetic Study of (9S)-9-Dihydroerythronolide A via Witting-Horner Coupling of C1-C6 and C7-C15 Segments
• Alternative Syntheses of the C9-C15 and C1-C5 Segments of Erythronolide A via Regio- and Stereo-Selective Reductive Ring Opening of 2,3-Epoxy Alcohols
• 17 マクロリドのキラル合成 : 3.エリスロノリドAの全合成研究(その2)
• Highly Stereoselective Total Synthesis of Methynolide, the Aglycon of the 12-Membered Macrolide Antibiotic Methymycin. I. Synthesis of a Prelog-Djerassi Lactone-Type Chiral Intermediate from D-Glucose(Organic,Chemical)
• Studies on Glucuronosides of Heterocyclic Compounds. I. Studies on the Synthesis and Properties of 2-Pyridyl β-D-Glucopyranosiduronic Acid and Its O→N Rearrangement
• Reactions and Synthetic Applications of β-Keto Sulfoxides. X. Synthesis of Ellipticine Analogs modified at the 5-Position
• Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via [3,3] Sigmatropic Rearrangement
• P-46 海洋産ポリエーテルマクロリド、ハリコンドリンBの全合成研究(ポスター発表の部)
• Large Laboratory Scale Synthesis of (2S, 3S)-2-(4-Methoxybenzyloxy)-3,4-O-(3-pentylidene)-1,3,4-butantriol, a Versatile Chiral Building Block in Natural Product Synthesis
• Stereoselective Synthesis of Optically Active 4-Ethyl-3,5-dihydroxy-2-methylpentyl Derivatives. A Basic Building Block with Three Contiguous Chiral Centers of Polyether Antibiotics
• 24 海洋産ポリエーテルマクロリド、ハリコンドリンBの全合成研究(口頭発表の部)
• 光学活性な天然ホスト分子としてのポリエーテル抗生物質
• Sythesis of Erythronolide A via Direct Macrolactonization of a Conformationally Controlled Seco-acid with the Yamaguchi Reagent in the Presence of Dimethylaminopyridine
• 25 ポリエーテル抗生物質リソセリンの立体選択的全合成(口頭発表の部)
• Highly Stereocontrolled Total Synthesis of the Polyether Antibiotic Salinomycin. IV. Chemical Degradation of Salinomycin for the Structure Confirmation of Synthesic Key Intermediates
• Highly Stereocontrolled Total Synthesis of the Polyether Antibiotic Salinomycin. III. Total Synthesis of Salinomycin via Coupling of C1-C9,C10-C17,and C18-C30 Segments
• Highly Stereocontrolled Total Synthesis of the Polyether Antibiotic Salinomycin. II. Synthesis of Right (C18-C30) Segments from D-Glucose, D-Mannitol, and Ethyl L-Lactate
• Highly Stereocontrolled Total Synthesis of the Polyether Antibiotic Salinomycin. I. Synthesis of the Left (C1-C9) and Middle (C10-C17) Segments from D-Glucose
• 69 エリスロノリドAの改良合成(口頭発表の部)
• 62(PA2-2) ポリエーテル系抗生物質イソラサロシドAとラサロシドAの合成研究(ポスター発表の部)
• 71 イオノフォアポリエーテル抗生物質リリノマイシンの立体選択的合成
• Highly Stereoselective Total Synthesis of Tylonolide, the Aglycon of the 16-Membered Macrolide Antibiotic Tylosin. II. Total Synthesis of Tylonolide by Virtue of 4-Methoxybenzyl and 3,4-Dimethoxybenzyl Protection(Organic,Chemical)
• Highly Stereoselective Total Synthesis of Tylonolide, the Aglycon of the 16-Membered Macrolide Antibiotic Tylosin. I. Construction of the C-1-C-8 Chiral Centers(Organic,Chemical)
• Highly Stereoselective Total Synthesis of Methynolide, the Aglycon of the 12-Membered Macrolide Antibiotic Methymycin. II. Kinetic Acetalization and Synthesis of the Seco-Acid(Organic,Chemical)
• Synthetic Studies on Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 9. Synthesis of the C16-C36 Unit via Stereoselective Construction of the D and E Rings
• Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 7. Synthesis of Two C27-C36 Units via Construction of the F Ring and Completely Stereoselective C-Glycosylation Using Mixed Lewis Acids
• 58 マクロリドのキラル合成 : 4. メチノリドの全合成
• メルドラム酸の化学 : マロン酸エチルとの違いをとらえる
• Meldrum's Acid in Organic Synthesis. V. Versatile One-pot Synthesis of Indolepropionic Esters via Simultaneous Condensation of Three Different Carbon Components, Indole, Aldehydes and Meldrum's Acid
• 84 マクロライドのキラル合成 : 1. Tylonolide,Protylonolide及びMycinolide全合成を目的としたMethynolideの合成
• Synthesis of 12α and 12β-Carboxyestradiol Derivatives via the Thermal Elimination of β-Ketosulfoxide
• Synthesis of Macrocyclic Amides. Formation of a New Symmetric 36-Membered Tetramide Ring
• Highly Stereoselective Total Synthesis of Pikronolide, the Aglycon of the First Macrolide Antibiotic Pikroraycin. Crucial Role of Benzyl-Type Protecting Groups Removable by 2,4-Dichloro-5,6-dicyanobenzoquinone Oxidation(Organic,Chemical)
• Highly Stereoselective Total Synthesis of Methynolide, the Aglycon of the 12-Membered Macrolide Antibiotic Methymycin. III. An Efficient Synthesis of Methynolide(Organic,Chemical)
• 43 Wittig-Horner反応による閉環をキーステップとするマクロリド抗生物質の合成 : メチノリド・ピクロノリド・タイロノリドの高立体選択的合成
• 4 インドール側鎖の選択的酸化による酸化型ジケトピペラジン系アルカロイドの合成
• A Convenient Synthesis of Estrone and 11-Methylequilenines based on the Thermal Elimination of β-Ketosulfoxides

もっと見る 閉じる

スポンサーリンク