Bruckner Sebastian, Haase Robert G, Schobert Rainer
Organic Chemistry Laboratory, University Bayreuth, Universitaetsstr. 30, 95447, Bayreuth, Germany.
Chemistry. 2017 Apr 27;23(24):5692-5695. doi: 10.1002/chem.201701259. Epub 2017 Apr 10.
3-Acyltetramic acids derived from β-hydroxytyrosine are synthetically challenging. The first route to this structural motif, based upon a condensation between a Meldrum's acid conjugate bearing the acyl side chain, and a β-hydroxytyrosinate, N-protected by an ortho-nitrobenzyl group is presented. This group enables the Dieckmann cyclization of the resulting N-(β-ketoacyl)amino ester, after which it can be removed photolytically without compromising the delicate 3'-hydroxy group. This strategy was applied to the first total synthesis of the fungal metabolite F-14329 (1).
由β-羟基酪氨酸衍生而来的3-酰基四嗪酸在合成上具有挑战性。本文介绍了基于带有酰基侧链的丙二酸亚异丙酯共轭物与被邻硝基苄基保护的β-羟基酪氨酸酯之间的缩合反应来合成这种结构基序的第一条路线。该基团能使所得的N-(β-酮酰基)氨基酯发生迪克曼环化反应，之后可以通过光解将其除去，而不会影响到脆弱的3'-羟基。该策略被应用于真菌代谢产物F-14329（1）的首次全合成。
