(-) -N-メチルウェルウィットインドリノーンCイソチオシアネート全合成
Alexander D Huters1, Kyle W Quasdorf, Evan D Styduhar
1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Journal of the American Chemical Society
|August 9, 2011
まとめ
研究者らは,複雑な天然製品である (-) -N-メチルウェルウィットインドリノーンCイソチオシアネートの最初の完全合成を達成しました. 重要なステップには,インドリンサイクリングとニトロンの挿入が組み立ての組み立てとブリッジヘッドの炭素機能化のために含まれていました.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 自然製品合成 自然製品の合成
- 薬用化学 薬用化学について
背景:
- (-) -N-メチルウェルウィットインドリノーンCイソチオシアネートは,潜在的な生物学的活性を持つ複雑な天然製品です.
- 複雑な構造は,重要な合成課題を提示しています.
研究 の 目的:
- (-) -N-メチルウェルウィットインドリノンCイソチオシアネートの最初の完全合成を達成するために.
- 複雑な天然製品合成に適用できる新しい合成方法論を開発する.
主な方法:
- 合成は, [4.3.1]-バイサイクルコアを構築するためにインドリンサイクリング戦略を採用しました.
- C11ブリッジヘッドの炭素を機能化するために,末期の分子内ナイトレン挿入が使用されました.
主要な成果:
- (-) -N-メチルウェルウィットインドリノンCイソチオシアネートの最初の完全な合成が成功しました.
- 開発された合成経路は,インドリンサイクリングとナイトレン挿入の有効性を,複雑なエスカフォード構築に実証しています.
結論:
- 総合合成により, (-) -N-メチルウェルウィットインドリノーンCイソチオシアネート (C-isothiocyanate) が,さらなる生物学的評価のために利用可能になりました.
- この研究は,合成化学者のツールキットを拡張し,自然製品の複雑なアーキテクチャにアクセスできます.
関連する概念動画
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
Disubstituted Cyclohexanes: cis-trans Isomerism
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.


