Synthetic Access to 3-Substituted Pyroglutamic Acids from Tetramate Derivatives of Serine, Threonine, allo-Threonine, and Cysteine

J Org Chem. 2019 Aug 16;84(16):10257-10279. doi: 10.1021/acs.joc.9b01432. Epub 2019 Jul 29.

Abstract

A general route which provides direct access to pyroglutamates from tetramates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is reported. This work permits direct scaffold hopping from tetramate to substituted pyroglutamates. Some compounds in the library showed modest antibacterial activity against Gram-positive bacteria.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cysteine / chemistry*
  • Molecular Conformation
  • Pyrrolidonecarboxylic Acid / chemical synthesis*
  • Pyrrolidonecarboxylic Acid / chemistry
  • Serine / chemistry*
  • Stereoisomerism
  • Threonine / chemistry*

Substances

  • Threonine
  • Serine
  • Cysteine
  • Pyrrolidonecarboxylic Acid