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Updated: Mar 7, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

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マダンガミンA,C,Eの統合した全合成

Takahiro Suto1, Yuta Yanagita1, Yoshiyuki Nagashima1

  • 1Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

Journal of the American Chemical Society
|February 14, 2017
PubMed
まとめ

スキップされたダイエンのための新しいステレオダイバーゲント合成戦略は,水溶解とミギタ-コスギ-スティルのカップリングを使用して開発されました. この方法はすべてのステレオアイソマーにアクセスし,マダンガミンアルカロイドの全合成に使用されました.

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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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