Simple Approach to Optically Active Drimane Sesquiterpenes Based on Enzymatic Resolution
スポンサーリンク
概要
- 論文の詳細を見る
When the β-acyloxy esters (±)-10 and (±)-11 were exposed to the lipase OF-360 from Candida rugosa or immobilized lipase OF-360 in a water-saturated organic solvent, the hydrolyzed product (8aS)- was obtained in high chemical (40%) and optical (>99%ee) yields. The absolute structure of (8aS)-6 was confirmed by the fact that (8aS)-6 was converted into an authentic sample γ-keto nitrile (8aS)-17. Treatment of the diol (±)-12 with isopropenyl acetate in the presence of the lipase Godo E-4 from Pseudomonas sp. provided the unchanged (8aR)-12 (89%ee) in 42% yield.
- 公益社団法人日本薬学会の論文
- 1997-05-15
著者
-
AKITA Hiroyuki
School of Pharmaceutical Science, Toho University
-
Akita H
Toho Univ. Chiba Jpn
-
Akita Hiroyuki
School Of Pharmaceutical Science Toho University
-
NOZAWA Masako
School of Pharmaceutical Sciences, Toho University
-
Nozawa M
Graduate School Of Pharmaceutical Sciences Chiba University
-
野澤 雅子
School Of Pharmaceutical Science Toho University
-
Akita Hiroyuki
School Of Parmaceutical Sciences Toho University
-
SAOTOME Chikako
School of Pharmaceutical Sciences, Toho University
-
FUTAGAMI Yoshiko
School of Pharmaceutical Science, Toho University
-
MIYAMOTO Maiko
School of Pharmaceutical Science, Toho University
-
Futagami Yoshiko
School Of Pharmaceutical Science Toho University
-
Miyamoto Maiko
School Of Pharmaceutical Science Toho University
-
Saotome Chikako
School Of Pharmaceutical Science Toho University
関連論文
- P-22 酵素機能を利用する高立体選択的キラルシントンの合成とその天然物合成への応用(ポスター発表の部)
- Reaction of Methyl 4,5-Epoxy-(2E)-pentenoate with Arenes. I. A Facile Synthesis of 4-Aryl-5-hydroxy-(2E)-pentenoate Derivatives
- Total Synthesis of (±)-, (-)-, and (+)-Oudemansin X
- Formal Syntheses of N-Trifluoroacetyl-L-acosamine and N-Trifluoroacetyl-L-daunosamine from an Achiral Precursor, Methyl Sorbate
- Synthesis of Ozonolysis Products of Myxothiazol
- Enzymatic Hydrolysis of meso(syn-syn)-1,3,5-Triacetoxy-2,4-dimethylpentane and Acetylation of meso(syn-syn)-3-Benzyloxy-2,4-dimethylpentane-1,5-diol by Lipase
- A Synthesis of (2R, 4'R, 8'R)-α-Tocopherol (Vitamin E) Side Chain
- Synthesis of the Metabolites of 4-(2-Methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide (KRP-197/ONO-8025)
- Catalytic Properties for Naphthoquinones and Partial Primary Structure of Rabbit Heart Acetohexamide Reductase.
- Catalytic Properties for Naphthoquinones and Partial Primary Structure of Rabbit Heart Acetohexamide Reductase
- Carbonyl Reductase Purified from Rabbit Liver Is Not the Product of a Carbonyl Reductase Gene (RCBR5 or RCBR6)Cloned from the Rabbit Liver cDNA Libray.
- Carbonyl Reductase Purified from Rabbit Liver Is Not the Product of a Carbonyl Reductase Gene (RCBR5 or RCBR6) Cloned from the Rabbit Liver cDNA Library
- Characterization of Acetohexamide Reductases Purified from Rabbit Liver, Kidney, and Heart: Structural Requirements for Substrates and Inhibitors
- Purifiation and Catalytic Properties of a Novel Acetohexamide-Reducing Enzyme from Rabbit Heart
- Synthesis of Decalin Type Chiral Synthons Base on Enzymatic Function
- Enantioselective Synthesis of (2R, 4'R, 8'R)-α-Tocopherol (Vitamin E) Based on Enzymatic Function
- Stereoselective Reduction of Acetohexamide in Cytosol of Rabbit Liver
- Reaction of Methyl 4,5-Epoxy-(2E)-pentenoate with Arylcopper Reagents
- Chemoenzymatic Synthesis of Sacranosides A and B
- Chemoenzymatic Synthesis of Naturally Occurring Benzyl 6-O-Glycosyl-β-D-glucopyranosides
- Simple Synthesis of β-D-Glycopyranosides Using β-Glycosidase from Almonds
- NITIDASIN, A NOVEL SESTERTERPENOID, FROM THE PERUVIAN FOLK MEDICINE "HERCAMPURI" (GENTIANELLA NITIDA)
- Concise Syntheses of Coronarin A, Coronarin E, Austrochaparol and Pacovatinin A
- Synthetic Study of Piericidins. II. Synthesis of Piericidin Analogues
- Synthetic Study of Piericidins. I. Synthesis of the Side Chain of Piercidin B_1
- A Novel Sesterterpenoid, Nitiol, as a potent Enhancer of IL-2 Gene Expression in a Human T Cell Line, from the Peruvian Folk Medicine"Hercumpuri" (Gentianella nitida)
- Determination of the Absolute Stereostructure of seco-Macrosphelide E Produced by a Fungal Strain from a Sea Hare
- Six New Constituents from an Ascomycete, Chaetomlum quadrangulatum, Found in a Screening Study Focused on Monoamine Oxidase Inhibitory Activity
- Concise Syntheses of Cystothiazoles A, C, D, and Melithiazol B
- Enzymatic Synthesis of (-)- and (+)-Acetoxyhexamides and (-)- and (+)-Hydroxyhexamides
- The Reaction of (4R, 5R)-and (4S, 5S)-4, 5-Epoxy-2(E)-Hexenoates and Secondary Amines
- The Reaction of 4,5-Epoxy-2(E)-hexenoate and Secondary Amines, Total Synthesis of (-)-Osmundalactone and (-)-Forosamine
- An Amphiphile-Lipase Aggregate Bearing 1,2-Dialkylated Mannitol Ether as a New Type of Immobilized Enzyme in Organic Solvents
- Simple Approach to Optically Active Drimane Sesquiterpenes Based on Enzymatic Resolution
- Enzymatic Hydrolysin in Organic Solvents for Kinetic Resolution of Water-Insoluble α-Acyloxy Esters with Immobilized Lipases
- Synthesis of (R)-Curcumene and (R)-Xanthorrizol Based on 1,2-Aryl Migration via Phenonium Ion
- Solvolysis of (4,5)-anti-4-Aryl-5-tosyloxy-2(E)-hexenoate Derivatives
- Enzymatic Resolution of (±)-5-Acetoxy-4-aryl-(2E)-pentenoate Derivatives
- The First Synthesis of (S)-(+)-Cacalol
- Five New Chromones Possessing Monoamine Oxidase Inhibitory Activity from an Ascomycete, Chaetomium quadrangulatum
- Synthesis of Methyl 1-O-(4-Hydroxymethamphetaminyl)-α-D-glucopyranouronate
- (1-Ethoxyvinyl)lithium in the Total Synthesis of Thymine Polyoxin C and Uracil Polyoxin C
- Chemoenzymatic Synthesis of n-Hexyl and ο-β-D-Xylopyranosyl-(1→6)-β-D-glucopyranosides
- First Synthesis of (+)-α-and (+)-γ-Polypodatetraenes
- Stereoselective Synthesis of 4'-α-Alkylcarbovir Derivatives Based on an Asymmetric Synthesis or Chemoenzymatic Procedure
- Total Synthesis of(S)-(+)-Curcudiol, and(S)-(+)-and(R)-(-)-Curcuphenol
- Formal Total Synthesis of (+)-Macrosphelide A Based on Regioselective Hydrolysis Using Lipase
- Isolation of (S)-N-feruloyl Normetanephrine from Achyranthes fauriei and Determination of Its Absolute Configuration
- Chemoenzymatic Synthesis of (+)-α-Polypodatetraene and Methyl (5R,10R,13R)-Labda-8-en-15-oate
- Enantioselective Reaction of (±)-1-Hydroxy-5-methyl-3-vinylcyclohex-2-ene and Its Acyl Derivatives Using Lipid-Lipase Aggregates in Organic Solvent
- Determination of the Absolute Structure of (+)-Cystothiazole B