L-Proline is a natural amino acid playing an important role in drug discovery as a cheap chiral bifunctional building block. In this context, over the past decade unnatural analogues of Proline also became extremely popular. For example, in 2010 Gilead launched Ledipasvir – a drug bearing the residues of two unnatural analogues of L-Proline. In this work, we have rationally designed, synthesized and applied a library of novel/previously scarcely available analogues of Proline in medicinal chemistry. Details of the synthesis and application of the obtained compounds will be discussed.1-9 1 V. Kubyshkin et al. Org.Biomol.Chem. 2015, 13, 3171. 2 A. Tymtsunik et al. Tetrahedron Lett. 2014, 53, 3847. 3 V. Kubyshkin et al. Org. Lett. 2012, 14, 5254. 4 I. Kondratov et al. Org.Biomol.Chem. 2012, 10, 8778. 5 P. Mykhailiuk et al. Tetrahedron 2011, 67, 3091. 6 V. Kubyshkin et al. Synthesis 2009, 3327. 7 P. Mykhailiuk et al. Angew.Chem.Int.Ed. 2008, 47, 5765. 8 V. Kubyshkin et al. Tetrahedron Lett. 2007, 48, 4061. 9 O. Grygorenko et al. Tetraheron: Asymm. 2006, 17, 252.

Synthesis and application of unnatural proline analogues: advanced building blocks for medicinal chemistry

251st National Meeting (2016)

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