35 (±)-Colchicineの生合成的全合成
スポンサーリンク
概要
- 論文の詳細を見る
A successful approach to the total synthesis of d,l-colchicine, patterned after biogenetical scheme by Robinson and Anet hypothesis, was made. Starting from 4,3'-diacetoxy-3,4',5'-trimethoxy-chalcone 9, after two step reduction compound 11 was oxidized by FeCl_3 to yield phenol coupling product, a spiro-dienone 12 in good yield. Partial reduction of the dienone 12 yield spiro-enone 15. The reaction of iodomethyl zinc iodide with compound 15 followed by Jones oxidation cyclopropane deriv. 24 was obtained. The successfull conversion 24 to 25 and 26 was done by acid treatment, in which the cyclopropane cleavage followed by aryl rearrengement are take place successively. Compound 25 and 26 could be easily convert to the tropolone 28 which was already synthesized by A. E. Eschenmoser and transformed to d,l-cochicine. The expecting final reaction to the total synthesis, cycloheptenone 27 to the tropolone 28 is now under the investigation.
- 天然有機化合物討論会の論文
- 1968-09-20
著者
関連論文
- OXYGENATION OF BIPHENYL BY THE REAGENT SYSTEM Fe(MeCN)^_6-H_2O_2-Ac_2O : AN IMPLICATION TO THE MECHANISM IN MAMMALIAN METABOLISM(Communications to the Editor)
- 医療薬学と有機化学の接点
- Non-enzymatic Oxygenation of (+)-Camphor Catalyzed by Iron(II) Acetonitrile Solvate
- Oxygenation of Olefinic Hydrocarbons Catalyzed by Iron(II) Acetonitrile Solvate
- Synthesis of Oxazoles by the Reaction of Ketones with Iron(III) Solvates of Nitriles
- A New Combined Oxidizing Reagent System, Fe (CH_3CN)^_6-IO^-_4 : Oxidation of Paraffin Hydrocarbons
- Oxygenation of Aromatic and Aliphatic Hydrocarbons by a New Reagent System, Fe (CH_3CN)^_6-H_2O_2-Ac_2O : An Effective Model Reagent for Mono-oxygenase
- Preparation and Reactivities of Hexakisacetonitrile Iron (III) Perchlorate and Related Complexes as Strong Oxidizing Reagents
- Differential Induction of Hepatic and Renal Microsomal Cytochrome P450 by N-Phenylalkylimidazoles in Rats
- A SPECIES REACTIVE WITH NITRATE ORGANIC SUBSTRATES IS GENERATED BY ANODIC OXIDATION OF REPCHLORATES IN ACETONITRILE
- A Convenient and Mild Dethioacetalization Method Using Fe(bpy)_3(ClO_4)_3・3H_2O
- Application of Iron(III) Complexes, Tris(2,2'-bipyridyl)iron(III) Perchlorate and Some Iron(III) Solvates, for Oxidative Aryl-Aryl Coupling Reactions
- 52 β-ポリケトンの合成を指向したエナミンとピロンの反応およびその展開によるイソクマリン類の生合成的合成
- 14 新しい鉄錯体〔Fe(DMF)_3Cl_2〕〔FeCl_4〕と酸化的カップリング反応
- Regio-Related Differential Induction of Hepatic Microsomal Heme Oxygenase and Cytochrome P450 by Substituted Imidazole and Pyridine Compounds in Rats
- 酸化酵素機能モデル鉄錯体の開発研究
- OXYGENATION OF METHYL CYCLOHEXYLPHENYLGLYCOLATE, A CONSTITUTIONAL UNIT OF DRUGS, CATALYSED BY IRON(II) ACETONITRILE SOLVATE
- Biomimetic Synthesis of Podophyllum Lignans
- New Reagent Systems Containing CrO_3 Provide Precursors for Syntheses of Neo-lignans
- 65 新しい酸化剤系CrO_3-HBF_4-CH_3CNを用いたネオリグナン類の生合成を模した合成研究
- 35 (±)-Colchicineの生合成的全合成
- 電解反応装置
- 40 アルカロイド合成における電解酸化法の応用 : (±)-Oxomaritidine,(±)-Oxocrinine,(±)-Flavinantine,(±)-Pallidine,(±)-Amurine,(±)-Cryptopleurine等の全合成