Heterocyclic Prostaglandins. III. Synthesis of 10-Oxa-11-deoxyprostaglandin E_2
スポンサーリンク
概要
- 論文の詳細を見る
The decarboxylation of various 1-substituted-3,7-dioxabicyclo[3.3.0]octane-2,8-diones (2b-j) was in vestigated. On treatment with potassium acetate in aqueous pyridine under reflux, all the compounds (2b-j) examined were decarboxylated in high yields to give the corresponding trans-3-hydroxymethyl-4-butanolides (3b-j). The synthesis of 10-oxa-11-deoxyprostaglandin E_2 (1a) from the compounds 3i and 3j is also described. The Moffatt oxidation of 3i and the Wittig reaction of the resulting aldehyde (6a) with dimethyl 2-oxoheptylphosphonate gave an enone (7a), which was converted into 10-oxa-11-deoxyprostaglandin E_2 methyl ester (8a) and the C_<15>-epimer (9a) by NaBH_4 reduction. Hydrolysis and subsequent relactonization of 8a gave 1a in 88% yield. A similar treatment of 9a gave 1b in 87% yield. Using a similar sequence of reactions, 1a and 1b were also prepared from the nitrile analog 3j via 8b and 9b.
- 社団法人日本薬学会の論文
- 1980-03-25
著者
-
石田 昭彦
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
-
日水 順一
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
-
日水 順一
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
関連論文
- Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides : Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams
- Synthesis of C-Nor Emetine Pyman
- Synthesis of 1,2,3,4-Tetrahydro-β-carboline Derivatives as Hepatoprotective Agents. I. Dithiocarbamates of Several α-Amino Acids(Medicinal Chemistry,Chemical)
- Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. IV. Modification of the Phenylpiperazino Moiety of 2-(Phenylpiperazino-alkoxyphenyl)thiazolidine-3-carbothloamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)
- Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. II. 2-(Phenylpiperazinoalkoxyphenyl)thiazolidine-3-thioearboxamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)
- Synthesis of 3,4-Dihydro- and 1,2,3,4-Tetrahydroisoquinolines
- A New Method for the Preparation of 3,4-Dihydro- and 1,2,3,4-Tetrahydro-β-carbolines
- A NEW METHOD FOR THE PREPARATION OF 3,4-DIHYDRO AND 1,2,3,4-TETRAHYDRO-β-CARBOLINES
- Syntheses of Substituted L- and D-Tryptophans
- A NEW METHOD FOR THE PREPARATION OF 3,4-DIHYDRO-β-CARBOLINES
- Heterocyclic Prostaglandins. VI. Synthesis of 11-Deoxy-8,10-diazaprostaglandin E_1 and Its 10-Methyl Derivative
- Heterocyclic Prostaglandins. V. Synthesis of (12R, 15S)-(-)-11-Deoxy-8-azaprostaglandin E_1 and Related Compounds
- Heterocyclic Prostaglandins(第4報)8-Aza-11-deoxyprostaglandin E_1およびその関連化合物の合成
- Heterocyclic Prostaglandins. III. Synthesis of 10-Oxa-11-deoxyprostaglandin E_2
- Heterocyclic Prostaglandins. II. An Effective Synthesis of 3,7-Dioxabicyclo [3.3.0] octane-2,8-dione and Its C_1-Substituted Derivatives
- Synthesis of 10-Oxa-11-deoxyprostaglandin E_1
- Studies on Conformation and Reactivity. VI. The Reduction Reaction of Cholesta-3,5-dieno [3,4-b] oxathiane with Lithium in Liquid Ammonia. The Characterization of Unique Ultraviolet Absorption of the 3,5-Dieno [3,4-b] oxathiano System
- The Polyphosphoric Acid-Catalyzed Ring Opening of 4,5-Epoxy-3-oxo Steroids. IV. The Synthesis of 17α-Hydroxy-4-ethylthiopregn-4-ene-3,20-dione and Its Analogs
- B-Homoprogesterone