Divergent synthetic routes to biologically relevant types of compounds: chiral polyfunctional γ-lactams and amino acids

TETRAHEDRON

卷:70

Article

Aguilera, Jordi¹  Moglioni, Albertina¹  Mor, Alex¹  Ospina, Jimena¹  Illa, Ona¹  Ortuno, Rosa M.¹ 

[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

关键词: gamma-Lactams;    Amino acids;    (-)-(S)-Verbenone;    Divergent synthesis;    Polyfunctional scaffolds;    Chirality;   

DOI  :  10.1016/j.tet.2014.07.011

来源: Elsevier

【 摘 要 】

Divergent and versatile synthetic routes leading to the title compounds are described. They start from a common chiral precursor derived from (-)-(S)-verbenone and afford polyfunctional gamma-lactams and gamma-and epsilon-amino acids. The cyclobutane moiety in these molecules acts as a chiral and polyfunctional platform providing stereogenic centres with unambiguous absolute configuration that control the chirality of the newly produced asymmetric carbons. Furthermore, it affords functional groups and carbon chains suitable not only to create the basic skeleton of the desired products but additional functional groups. These features confer on these derivatives a great versatility for further uses in the development of new drugs and as synthetic building blocks. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free