Synthetic Studies on Lythraceae Alkaloids. III. Stereoselective Total Synthesis of (±)-Decaline
スポンサーリンク
概要
- 論文の詳細を見る
The first stereoselective total synthesis of one of Lythraceae alkaloids, decaline, was described. The Mannich condensation of isopelletierine (III) with 6-bromoisovanillin (IV) afforded stereoselectively the trans quinolizidine (V) which was converted to the methyl ether (VI). Stereoselective reduction of VI with the Henbest catalyst gave the axial alcohol (VII) along with the equatorial alcohol (VIII). The Ullmann condensation of the acetyl derivative (IX) from VII with the ester (XI) furnished the biphenyl ether (XII). Hydrolysis of XII and lactonization of the resulting hydroxy-acid (XIV) provided (±)-decaline (II).
- 社団法人日本薬学会の論文
- 1975-09-25
著者
-
小川 信男
Faculty Of Pharmaceutical Sciences Kanazawa University
-
荒田 義雄
Faculty Of Pharmaceutical Sciences Kanazawa University
-
花岡 美代次
Faculty of Pharmaceutical Sciences, Kanazawa University
-
花岡 美代次
金沢大学薬学部
-
花岡 美代次
Faculty Of Pharmaceutical Sciences Osaka University
-
花岡 美代次
Faculty Of Pharmaceutical Sciences Kanazawa University
関連論文
- 1-Azabicyclo化合物の研究(第8報) : Octahydropyrrocolineから9員環状アミンの合成
- Studies on Antispasmodics. VI. Synthesis of N-Alkyl 6- and 7-Diarylmethyleneindolizidinium Bromides
- Studies on Antispasmodics. V. Synthesis and Anticholinergic Activity of N-Alkyl 1- and 2-Diarylmethylene-indolizidinium Bromides
- Studies on 1-Azabicyclo Compounds. XXVI. Synthesis of Ten-membered Ring Amines from 9a-Cyanomethyl-, 9a-Ethoxycarbonylmethyl-, and 1-Ethoxycarbonyl-octahydroquinolizine
- 4 Securinine及びVirosecurinineの全合成
- Total Synthesis of Securinine
- Studies on 1-Azabicyclo Compounds. XXVIII. Synthesis of 1-Methyl-perhydroazocin-5-one from Pyrrolizidine
- Synthesis of (±)-Methyldecamine
- Erythro-Selective Aldol Reaction of Tricarbonyl(η^6-o-trialkylsilylbenzaldehyde)chromium(0) Complexes with Cyclic Ketene Silyl Acetals
- Chemical Transformation of Protoberberines. XVII. Biomimetic Introduction of an Oxy Functionality at the C-10 Position in the Benzo[c]phenanthridine Skeleton : Synthesis of 2,3,7,8,10-Pentaoxygenated Benzo[c]phenanthridine Alkaloids, Chelilutine and Sangu