Głowacka Iwona E, Trocha Aleksandra, Wróblewski Andrzej E, Piotrowska Dorota G
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland.
Beilstein J Org Chem. 2019 Jul 23;15:1722-1757. doi: 10.3762/bjoc.15.168. eCollection 2019.
Since Garner's aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of -(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted -(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.
由于加纳醛有几个缺点,首先它容易发生外消旋化,因此替代的三碳手性源在天然化合物和/或药物的对映选择性合成中具有重要价值。这篇综述文章总结了-(1-苯乙基)氮杂环丙烷-2-羧酸酯、-醛和-甲醇在已批准药物、潜在药物以及天然产物(主要是生物碱,但也包括鞘脂类和神经酰胺及其1-和3-脱氧类似物)和几种羟基氨基酸及其前体的合成中的应用。所设计的策略为几种药物提供了新的合成方法,并为天然产物提供了替代方法,证明了2-取代的-(1-苯乙基)氮杂环丙烷骨架作为带有手性助剂的手性源的有效性。