Synthesis of terminally protected (S)-β³-H-DOPA by Arndt–Eistert homologation: an approach to crowned β-peptides

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• 作者：Gaucher ; Anne ; Dutot ; Laurence ; Barbeau ; Olivier ; Hamchaoui ; Wahib ; Wakselman ; Michel ; Mazaleyrat ; Jean-Paul
• 刊名：Tetrahedron ; Asymmetry
• 出版年：2005
• 期刊代码：108_09574166
• 类别：ch
• 出版时间：February 21, 2005
• 卷：16
• 期：4
• 页码：857-864
• 文件大小：193 K

摘要

Terminally protected Boc-(S)-脦脦³-H-DOPA-OMe has been synthesized from l-DOPA by the Arndt脦脦脦Eistert homologation procedure. During the synthesis, the side-chain catechol group was temporarily protected by benzylation. The absence of racemization was demonstrated by ¹⁹F NMR analysis of the (+)-(R)- and (脦脦脦)-(S)-脦脦-methoxy-脦脦-trifluoromethyl-脦脦-phenyl-acetamide derivatives. The catechol function of Boc-(S)-脦脦³-H-DOPA-OMe may be used for crown-ether formation, a step towards the construction of crowned 脦脦-peptides.