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

スポンサーリンク

概要

• 論文の詳細を見る

• (S)-4[(2R, 5R, 6S)-5-Ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl]pentan-4-olide (5), an alkaline degradation product of salinomycin (1), was synthesized with complete stereoselectivity from D-mannitol and ethyl L-lactate.Compound 5 was then converted to (3R, 4S, 7S)-7-[(2R, 5R, 6S)]-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl]-4,7-bismethoxymethoxy-3-(tetrahydropyran-2-yloxy)oct-1-yne (3), a C18-C30 segment of 1,via Sharpless asymmetric epoxidation. Another C18-C30 segment, (R)-3-[2RS, 5S]-5-[(2R, 5R, 6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-2-methoxy-5-methyltetrahydrofuran-2-yl]-3-(4-methoxybenzyloxy)prop-1-yne (4), was synthesized more conveniently via coupling between a C19-C22 fragment prepared starting from D-glucose and a C23-C30 fragment prepared starting from D-mannitol and ethyl L-lactate.

• 公益社団法人日本薬学会の論文
• 1989-07-25

著者

• 及川 裕二

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 米光 宰

  岡山理大理

• 米光 宰

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 及川 裕二

  北大薬

• 米光 宰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 堀田 清

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 長戸 哲

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 堀田 清

  Faculty Of Pharmaceutical Sciences Health Science University Of Hokkaido

• 長戸 哲

  Faculty Of Pharmaceutical Sciences Hokkaido University

関連論文

• P-43 16員環マクロリド・ヒグロリド類の全合成研究(ポスター発表の部)
• 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)
• Photochemical Synthesis of 1,2,3,4-Tetrahydroisoquinolin-3-ones and Oxindoles from N-Chloroacetyl Derivatives of Benzylamines and Anilines. Role of Intramolecular Exciplex Formation and cis Conformation of Amide Bonds
• 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
• 3-METHOXYBENZYL (3-MPM) ABD 3,5-DIMETHOXYBENZYL (3,5-DMPM) PROTECTING GROUPS FOR THE HYDROXY FUNCTION LESS READILY REMOVABLE THAN 4-METHOXYBENZYL (MPM)AND 3,4-DIMETHOXYBENZYL (DMPM) PROTECTING GROUPS BY DDQ OXIDATION
• Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via [3,3] Sigmatropic Rearrangement
• PHOTOCHEMICAL SYNTHESIS OF ANTITUMOR PLATINUM PYRIMIDINE GREENS ; POSSIBLE CONTRIBUTION OF SINGLET OXYGEN(Communications to the Editor)
• 20.Aspidosperma及びIboga alkaloidsの合成研究
• 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)
• 41 14員環マクロリドのセコ酸誘導体の立体配座計算とマクロラクトン化(口頭発表の部)
• 51 高立体選択的ヘテロジールスアルダー反応の開発とポリアミン系アルカロイドカンナビサチビンの合成への応用(口頭発表の部)
• マクロリドの合成--高い選択性と効率をもった易しい合成法を確立するために
• 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
• 22.Aspidosperma alkaloidsの合成研究
• The Absolute Configuration of Sarkomycin.
• 25 天然物の絶対配置に関する研究 : エメチン、ヨヒンピン、レセルピンに就いて
• Extremely Mild and Selective Method for Hydrolysis of Tosyl Esters by Photo-Sensitized Single Electron Transfer Reactions
• DEPROTECTION OF BENZYL TYPE PROTECTING GROUPS FOR HYDROXY FUNCTIONS BY A PHOTO-INDUCED SINGLE ELECTRON TRANSFER REACTION
• 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)
• On a Novel System for the Photosensitized Water Reducaion Which Contains the Iron-Sulfur Cluster, (Et_4N)_2 [Fe_4S_4 (SBzl)_4]
• Quinolizidines. VII. Structure of O-Methylpsychotrine : The Endocyclic versus the Exocyclic Double Bond Structure in the Dihydroisoquinoline Moiety
• Photochemical Synthesis of Azepinoindoles and Azocinoindoles from N-Chloroacetylindolylethylamines, and a Mechanistic Study based on the Correlation between Quantum Yields and Calculated Frontier Electron Densities of Indole Radicals
• Singlet and Triplet Excited State Photochemistry of Tricyclo-[5. 2. 2. 0^] undeca-3,10-dien-9-one Derivatives
• Photoalkylation of Aromatic Amino Acids as a Model of Photochemical Modification of Protein with Chloroacetamide
• Photocyclization of N-Chloroacetyl-2,5-dimethoxyphenethylamine. Synthesis of Pyrroloindoles
• Cage Effect for the Photochemical Formation of the Ten-Membered Lactam from N-Chloroacetyl-3-methoxyphenethylamine
• The Preparation and Chemical Reactions of a Peracid Resin
• Flash Photolysis of Allyl Phenyl Ethers
• Mechanism of Photocyclization of N-Chloroacetyl-m-tyramine A Flash Photolysis Study
• Infrared Spectra of Some Indole and Pyrrole Compounds
• Reaction of 1-Phenethyl-2 (1H)-pyridones with Phosphoryl Chloride. Formation of 1-Phenethyl-2-chloropyridinium Salts.
• Stereoselective Total Synthesis of 16-Membered Macrolide Aglycons, Leuconolides and Maridonolides. Macrocylic Stereocontrol Based on Conformational Analysis of the 16-Membered Macrolide Ring
• 4-Azabicyclo [5,2,2] undeca-8,10-dien-3-ones. Photochemical Formations and Novel Rearrangements
• 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
• 1.ヨヒンビンの絶対配置とオキシインドール系アルカロイドとの関係
• 31 環上での立体制御反応を利用した16員環マクロリド類の合成(口頭発表の部)
• Polyphosphate Esters as a Synthetic Agent. III. Amide and Peptide Syntheses
• 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
• 113(P-42) 抗腫瘍活性18員環マクロリド・テダノリドの全合成研究(ポスター発表の部)
• Synthesis of Macrocyclic Amides. Formation of a New Symmetric 36-Membered Tetramide Ring
• Facile Total Synthesis of Carbonolides by Witting-Hoener Macro-Cyclization and Stereoselective Epoxidation
• マクロリド合成
• マクロリドの合成 : 高い選択性と効率をもった易しい合成法を確立するために
• 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
• Photo-rearrangements of Methyl Indole-1-acetate, Indole-1-acetamide and Methyl Indoline-1-acetate
• Photo-induced Friedel-Crafts Reactions. IV. Indoleacetic Acids
• Photo-induced Friedel-Crafts Reaction. II
• 3H-Indoles. IV. Photo-and Peroxide-induced Oxygenation of 2-Ethyl-3H-indoles
• Polyphosphate Ester as a Synthetic Agent. XIII. Syntheses of 2-Substituted Benzoxazoles and Benzthiazoles with PPE
• Polyphosphate Ester as a Synthetic Agent. XI. Synthesis of 2-(1'-Aminoalkyl) benzimidazoles from N-Benzoylamino Acids
• Selective Reduction of Peptide-ester Groups in Aqueous Solution
• Polyphosphate Ester as a Synthetic Agent. VII. The Beckmann Rearrangement and Formation of Amidines with PPE
• Polyphosphate Ester as a Synthetic Agent. IV. A Novel Preparation of Aryl Esters
• Polyphosphate Ester as a Synthetic Agent. V. The Fischer Indole Synthesis with Polyphosphate Ester
• 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
• Photocyclization of N-Chloroacetyl-3-methoxyphenethylamine and N-Chloroacetyl-3,5-dimethoxyphenethylamine.
• Selective Reduction of Peptide-ester Groups in Aqueous Solution III. Valine and Proline Esters
• Esterification of Model Peptides in Aqueous Solution
• 112(P48) 紅藻由来の環状ポリケタイド化合物の合成研究(ポスター発表の部)
• Preliminary Studies on the Stereochemistry of Emetine. II. Ultraviolet and Infrared Absorption Spectra of 3,4-Dihydroisoquinoline and its Homologs
• Preliminary Studies on the Stereochemistry of Emetine. I. Mercuric Acetate Dehydrogenation of (-)-2'-Acylemetines
• Polyphosphate Esters as Synthetic Reagent. I. Synthesis of 2-Substituted Benzimidazoles
• The Enamine-Immonium Cation System of 9,10-Dimethoxy-1,2,3,4,6,7-hexahydrobenzo [a] quinolizinium Salt

もっと見る 閉じる

スポンサーリンク