Lipase-catalyzed synthesis of ethyl (R)-2-benzyloxy-2-isopropylhydrogenmalonate: a useful combination of chemical synthesis with enzymatic methods

Biosci Biotechnol Biochem. 2019 Apr;83(4):763-767. doi: 10.1080/09168451.2018.1554426. Epub 2019 Jan 17.

Abstract

Ethyl (R)-2-benzyloxy-2-isopropylhydrogenmalonate is a key intermediate for the synthesis of the side chain in ergopeptines. In this work, we adopted a method to prepare enantiomerically pure title monoester via immobilized Candida antarctica lipase B (Novozym 435)-catalyzed hydrolysis of the corresponding diester.

Keywords: Ergot alkaloids; Ethyl ()-2-benzyloxy-2-isopropylhydrogenmalonate; Lipase; Novozym 435; hydrolysis.

MeSH terms

  • Biocatalysis
  • Dihydroergotoxine / chemical synthesis*
  • Dihydroergotoxine / metabolism
  • Enzymes, Immobilized / chemistry
  • Fungal Proteins / chemistry*
  • Hydrolysis
  • Lipase / chemistry*
  • Malonates / chemical synthesis*
  • Malonates / metabolism
  • Solvents / chemistry
  • Stereoisomerism

Substances

  • Enzymes, Immobilized
  • Fungal Proteins
  • Malonates
  • Solvents
  • Dihydroergotoxine
  • Lipase
  • lipase B, Candida antarctica