A Linchpin Synthesis of 6-Hydroxyceramides from Aziridine Aldehydes
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- 作者：Sean. K. Liew ; Sherif J. Kaldas ; Andrei K. Yudin
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：December 16, 2016
- 年：2016
- 卷：18
- 期：24
- 页码：6268-6271
- 全文大小：362K
- ISSN：1523-7052
文摘
A chemoselective N-oxidation/Meisenheimer rearrangement protocol was developed to generate vinylaziridine scaffolds from aziridine aldehydes. A subsequent Lewis acid-mediated aziridine ring opening with carboxylic acid nucleophiles followed by N–O bond cleavage furnishes a human skin 6-hydroxyceramide natural product in short order. The utility of this methodology is demonstrated by the preparation of a number of unnatural 6-hydroxyceramide analogues. This modular approach enables the expedient synthesis of poorly understood skin lipids, which may find application in therapeutics and cosmetics.