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Proline Methanologues: Design, Synthesis, Structural Properties, and Applications in Medicinal Chemistry

  • Miguel Angel Vilchis-Reyes
  • Stephen Hanessian
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 48)

Abstract

In this review, we discuss methanoprolines, which are analogues of proline that contain a bridged methylene group at different positions, which we designate herein as proline methanologues. Particular emphasis is placed on naturally occurring members, general methods for the stereocontrolled synthesis of different diastereoisomers, functionalized analogues, conformational and stereoelectronic features, as well as their utility as proline congeners in medicinally relevant compounds.

Keywords

Conformational analysis Constrained amino acids Drug prototypes Natural products 

Notes

Acknowledgements

We thank CONACyT for a fellowship to Miguel Vilchis and to NSERC for financial support.

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  • Miguel Angel Vilchis-Reyes
    • 1
  • Stephen Hanessian
    • 1
  1. 1.Department of ChemistryUniversité de MontréalStation Centre-ville, MontréalCanada

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