The Regioselective Dehydration of Unsymmetrical Secondary Alcohols under Mitsunobu's Reaction Conditions
スポンサーリンク
概要
- 論文の詳細を見る
Dehydration of the four diastereomers of tetrahydropyran 8-11 involving the 4-hydroxyl and 5-methyl groups with diethylazodicarboxylate-PPh_3-toluene was undertaken to clarify the relation between the configurations of these substituents and the direction of dehydration. Compound 8 with 4β(equatorial)-hydroxyl and 5β(axial)-methyl groups was found to give the trisubstituted olefin 12 exclusively, and the isomers 13 and 14 were shown to be produced from 9 and 11,respectively, with high selectivity. The mechanisms involved are discussed.
- 社団法人日本薬学会の論文
- 1990-09-25
著者
-
山田 治民
Riken Institute (the Institute Of Physical And Chemical Research)
-
秋田 弘幸
Riken Institute (The Institute of Physical and Chemical Research)
-
松倉 弘子
Riken Institute (The Institute of Physical and Chemical Research)
-
中田 忠
Riken Institute (The Institute of Physical and Chemical Research)
-
大石 武
Riken Institute (The Institute of Physical and Chemical Research)
-
松倉 弘子
理研
-
大石 武
Faculty Of Engineering Yokohama National University:(present Address)meiji College Of Pharmacy
-
大石 武
理研:(現)明治薬科大学
-
中田 忠
東京理大・理
関連論文
- 77(P-73) デヒドロアルテヌシンの全合成と構造解析(ポスター発表の部)
- 28 ブレベトキシンBの全合成(口頭発表の部)
- The Regioselective Dehydration of Unsymmetrical Secondary Alcohols under Mitsunobu's Reaction Conditions
- ENZYMATIC HYDROLYSIS IN ORGANIC SOLVENTS FOR KINETIC RESOLUTION OF WATER-INSOLUBLE α-ACYLOXY ESTERS WITH IMMOBILIZED LIPASES
- 29 20員環マクロライド抗生物質、ベンツリシジンの合成研究(口頭発表の部)
- 99(P-34) 合成化学的手法を用いたMacroviracin類の絶対立体配置の決定(ポスター発表の部)
- 95(P-52) SmI_2を用いる環化反応を利用した抗腫瘍活性アセトゲニン、ムコシンの全合成(ポスター発表の部)
- 129(P-74) 抗腫瘍活性アセトゲニン、ジメネジンの全合成と構造改定(ポスター発表の部)
- 108(P38) 抗腫瘍活性物質ムコシンの全合成(ポスター発表の部)
- SYNTHETIC STUDY OF MARINE MACROLIDE SWINHOLIDE A. STEREOCONTROLLED SYNTHESIS OF THE C11-C32 SEGMENT
- 23 スウィンホライドAおよびその関連化合物の合成研究(口頭発表の部)
- 全合成の夢を語る
- 23 海産環状グアニジン天然物の全合成及びその化学的生物学的機能(口頭発表の部)
- The Synthesis of 3-Spirooxindole Derivatives. IX. The Reactions of 2-Hydroxytryptamine with Hemiacetals
- カイコへのアビエチン酸誘導体の経口投与による3眠蚕の出現
- 7 ベンゾニリデン型ジテルペンの転位反応
- 28 ヘミブレベトキシンBの全合成(口頭発表の部)
- 22 海洋産多環状エーテル天然物の合成研究(口頭発表の部)
- 77 マイカラミドAおよび関連化合物の合成研究(ポスター発表の部)
- 38 Reveromycin Aの全合成(口頭発表の部)
- A Facile Chemoenzymatic Route to Optically Active 4,5-Disubstituted-2E-hexenoate Derivatives. I
- Enantioselective Acetylation of an α-Hydroxy Ester by Using Ether-Linked Lipid-Lipase Aggregates in Organic Solvents
- A Formal Total Synthesis of (-)-Oudemansin B
- A Lipid-Lipase Aggregate with Ether Linkage as a New Type of Immobilized Enzyme for Enantioselective Hydrolysis in Organic Solvents
- A FACILE CHEMOENZYMATIC ROUTE TO ENANTIOMERICALLY PURE 4,5-DISUBSTITUTED-2-HEXENOATE DERIVATIVES
- A LIPID LIPASE AGGREGATE AS A NEW TYPE OF IMMOBILIZED ENZYME
- Asymmetric Reduction of α-Methyl β-Keto Esters by Microbial Cells Immobilized with Prepolymer(Organic,Chemical)
- 38 生体触媒を用いるキラルシントンの合成とその天然物合成への応用
- SYNTHESIS OF USEFUL CHIRAL SYNTHONS (2R, 3R)-2-METHYLMALATE AND ITS CONGENERS VIA MICROBIAL ASYMMETRIC REDUCTION
- ELECTRONIC EFFECTS ON THE REGIOSELECTIVITY IN THE REACTIONS OF THIOALLYLIC ANIONS WITH CARBONYL COMPOUNDS
- 22 リベロマイシンBの全合成(口頭発表の部)
- 102(P47) ポリエンマクロライドRK-397の構造決定(ポスター発表の部)
- Reduction of Nitroolefin Using Microorganisms
- Medium-Membered Ring Ketone Synsthesis. Synthesis of Oxa- and Aza-cyclooctanone Derivatives
- A Synthesis of (±)-Dihydrodeoxyepiallocernuine by Application of a Facile Hofmann-Loeffler Type of Photocyclization
- Microbiologically Modified Chiral Synthon. III. 4,9-Dimethyl-3,5-dioxo-Δ^-octalin for Formal Total Syntheses of Certain Sesquiterpenoids
- MICROBIOLOGICAL ASYMMETRIC INDUCTION OF 4,9-DIMETHYL-3,5-DIOXO-Δ^-OCTALIN
- Microbiologically Modified Chiral Synthon. II. : 4,9-Dimethyl-3,7-dioxo-Δ^-octalin for Formal Total Syntheses of Certain C(8) Oxygenated Sesquiterpenoids
- Microbiologically Modified Chiral Synthon. I. 3,8-Dioxo-4-methoxycarbonyl-9-methyl-Δ^-octalin for Formal Total Syntheses of Certain Sesquiterpenoids and Diterpenoids
- アリル=ジチオカルバメ-トとアルデヒドとの反応のレギオ選択性におよぼす添加物の影響 (ヘテロ原子の有機化学) -- (6族元素(硫黄,セレン,テルル))
- 37 中環状テルペン類の合成研究 : カリオフィレン類の全合成
- Chemical Synthesis of Deoxyribonucleotides Containing Deoxyadenosine at the 3'-End on a Polystyrene Polymer Support
- 2'- AND 3'-SUBSTITUTED SANGIVAMYCINS : CONFORMATIONAL RESTRICTION BY THE GAUCHE EFFECT
- Synthesis of (+)- and (-)-cis-α-Irones
- Studies on Taxane Synthesis III.Stereocontrolled Synthesis of a Twelve-Membered Lactam Sulfide as a Precursor of 4,8,11,11-Tetramethyl-3-oxobicyclo[5.3.1]undec-8-ene
- 「基礎科学特別研究員制度」設立に関連して想う
- 高選択的新規反応の開発と有用天然物合成への応用
- Studies on Taxane Synthesis. II. : Synthese of 3,8,11,11-Tetramethyl-4-oxo- and 4,8,11,11-Tetramethyl-3-oxo-bicyclo[5.3.1]undec-8-enes Corresponding to the A- and B-Rings of Taxane Diterpenes
- Studies on Taxane Synthesis. I. : Synthesis of 3,8,11,11-Tetramethyl-4-oxobicyclo[5.3.1]undecane as a Model for Taxane Synthesis
- エリスロマイシンA合成研究をめぐって
- オリゴヌクレオチド合成技術の進歩とヒト成長ホルモン遺伝子の合成
- Meta Functionalization of Anilines and Phenol
- Medium-ring Ketone Synthesis. Synthesis of Eight- to Twelve-membered Cyclic Ketones based on the Intramolecular Cyclization of Large-membered Lactam Sulfoxides or Sulfones
- Medium-ring Ketone Synthesis. Intramolecular Acylation of Sulfur-stabilized Carbanions : A Model Study
- A NEW SYNTHETIC METHOD FOR β, γ-UNSATURATED KETONES AND A TOTAL SYNTHESIS OF EGOMAKETONE
- 大環状ラクタムスルフィドの分子内閉環反応を基盤とする中環状化合物の合成 (中・大環状天然物合成の新展開) -- (炭素環状化合物の形成反応とテルペノイドおよびその関連化合物の合成)
- Forced Nucleophilic Substitution Reaction of Chlorobenzenes bearing Electron-Donating Groups by the Use of"Naked"Methoxide Anion
- Revised Stereostructure for (+)-Roemecarine and Synthesis of (±)-, (+)-, and (-)-Roemercarine and (±)-Epiroemecarine
- Kinetic Resolution of (±)-4-Acyloxy-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisopuinolines by Use of Immobilized Lipases in Organic Solvents
- The Reactions of Activated Amides. I. The Reactions of Iminoethers derived from the Secondary Amides with the Nucleophiles
- The Fischer Indole Synthesis with Formic Acid.I.A Convenient Synthesis of 4a-Ethyl-9-formyl-1,2,3,4,4a, 9a-hexahydro-9H-carbazole
- Asymmetric Reduction of 2-Aminobenzophenone Using Yeast, Rhodosporidium toruloides
- Activation of Weak Organic Bases. VI. The Alkylation of Thiol Esters by Triethyloxonium Salt and Diethoxycarbonium Salt (HC^^+(OC_2H_5)_2,S^^-bCl_6)
- Diterpenoids. XLV. Ozonolysis of Phenolic Dehydroabietic Acid Derivatives
- DETERMINATION OF THE STEREOSTRUCTURE OF THE δ-LACTONES OF 5,7-DIHYDROXY-2,3-UNSATURATED ACIDS BY ^1H NMR SPECTROSCOPY(Communications to the Editor)
- Formal Total Synthesis of (-(-Indolmycin
- A FORMAL SYNTHESIS OF l-α-SANTONIN FROM CHIRAL α, β-EPOXYEUDESMANOLIDE VIA ENZYME-CATALYZED HYDROLYSIS
- A Facile Chemoenzymatic Route to Optically Active 4,5-Disubstituted-2E-hexenoate Derivatives. II
- 微生物を利用する不斉還元
- A Total Synthesis of (±)-Warburganal
- 28 摂食阻止物質(±)-Warburgana/およびその関連化合物の全合成
- Diterpenoids. XLI. Rearrangement of Deisopropyl Phenacylidene Type Diterpene by Means of Aluminum Chloride
- Diterpenoids. XXXVII. Rearrangement of Methyl 13-Isopropyl-7-oxo-podocarpa-5,8,11,13-tetraen-15-oate by Means of Aluminum Chloride
- Diterpenoids. XXXI. Reaction of Methyl Dehydroabietate Derivatives with Aluminum Chloride under Effect of Electron-withdrawing Group. Synthesis of Methyl Deisopropyldehydroabietate Series
- Diterpenoids. XXX. Reaction of Methyl Dehydroabietate Derivatives with Aluminum Chloride under Effect of Electron-donating Group
- Diterpenoids. XXIX. Nitration of Methyl Dehydroabietate Derivatives
- Diterpenoids. XXVIII. Nitration of Methyl 7-Oxo-dehydroabietate Derivatives
- Novel Nitration Reaction of Methyl 7-Oxodehydroabietate
- 70 1,3-ポリオールの立体構造決定法の開発と関連天然物の合成 : ペンタマイシンの立体構造(口頭発表の部)
- P-28 酵素化学的炭素-炭素結合形成反応の開発と光学活性非糖質鍵中間体合成への応用(ポスター発表の部)
- Chemoenzymatic Carbon-Carbon Bond Formation Leading to Non-carbohydrate Derivative. Stereoselective Synthesis of Pentamycin C-11-C-16 Fragment
- Structural Characteristics of Lipid-Lipase Aggregates for Enantioselective Hydrolysis in Organic Solvents
- リパーゼを用いる光学活性ヒドロキシエステルの創製とその生理活性化合物合成への応用 : ベンツリシジンA, Bアグリコンの全合成
- The Reactions of Activated Amides. VI. The Reactions of 1-Methyl-2-pyrrolidone Dimethylacetal and 2-Methylmercapto-1-methyl-2-pyrroline with Dimethyl Acetylenedicarboxylate
- The Fischer Indole Synthesis with Formic Acid. II. The Synthesis of Hexahydrocyclopent (b) indoles
- The Synthesis of 3-Spirooxindole Derivatives. VIII. Total Syntheses of (±)-Formosanine, (±)-Isoformosanine, (±)-Mitraphylline and (±)-Isomitraphylline
- The Synthesis of 3-Spirooxindole Derivatives. VII. Total Synthesis of Alkaloids (±)-Rhynchophylline and (±)-Isorhynchophylline
- The Reactions of Activated Amides. V. The Reactions of Cyclic Amide Acetals with Electrophiles
- Activation of Weak Organic Bases. V. The Alkylation of Thiono Esters by Diethoxycarbonium Hexachloroantimonate [chemical formula], S^^-bCl_6
- Activation of Weak Organic Bases. III. The Reactions of Divalent Sulfides with Acid Chlorides in the Presence of Friedel-Crafts Catalysts
- The Reactions of Activated Amides. IV. The Reactions of Amide Acetals with Esters
- The Synthesis of 3-Spirooxindole Derivatives. IV. The Conversion of 3-Spirooxindole to Indole Derivative.
- The Synthesis of 3-Spirooxindole Derivatives. III. Stereospecific Syntheses of rac-N-Methylrhynchophyllane for Stereochemistry of Rhynchophylline and Isorhynchophylline.
- The Synthesis of 3-Spirooxindole Derivatives. II. Syntheses of 1-Methylspiro-[indoline-3,1'-pyrrolizidine and Indolizidine]-2-one.
- The Synthesis of 3-Spirooxindole Derivatives. I. Syntheses of 1-Methyl-2', 3', 10', 10'a-tetrahydrospiro [indoline-3,1' (5'H)-pyrrolo [1,2-b]-isoquinoline]-2-one and its Homologs.
- β-HYDROXY-δ-LACTONES AS CHIRAL BUILDING BLOCKS INVOLVING 1,3-DIHYDROXYL FUNCTIONS. 1. : NEW STRATEGIES FOR STREOSELECTIVE CONSTRUCTION OF 2-METHYL-3,5-DIHYDROXY ESTERS
- Highly syn-Selective Reduction of α-Phenylthio-β-methoxy Ketones with Super-hydride
- 17 鎖状立体制御を基盤としたエリスロマイシンAの形式全合成(口頭発表の部)
- 95 ポリエンマクロライド抗生物質ペンタマイシンの合成研究(口頭発表の部)
- 有機合成化学研究室--高選択的反応と天然物合成