Concise Synthesis of Both Enantiomers of Pilocarpine

Molecules. 2021 Jun 16;26(12):3676. doi: 10.3390/molecules26123676.

Abstract

Furan-2-carboxylic acid was used as a starting material for the synthesis of dehydro-homopilopic acid. Esterification, hydrogenation and enzymatic hydrolysis followed by the reduction of Weinreb amides and a single-step attachment of a 1-methyl-imidazole residue allowed for the concise synthesis of both enantiomers of pilocarpine.

Keywords: alkaloids; enzymatic resolution; pilocarpine.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • Amides / chemistry
  • Carboxylic Acids / chemistry
  • Esterification
  • Furans / chemistry*
  • Hydrogenation
  • Hydrolysis
  • Pilocarpine / chemical synthesis*
  • Pilocarpine / chemistry
  • Stereoisomerism

Substances

  • Amides
  • Carboxylic Acids
  • Furans
  • Pilocarpine
  • homopilopic acid
  • 4-Butyrolactone
  • 2-furoic acid