Synthesis of (-)-berkelic acid

Angew Chem Int Ed Engl. 2009;48(7):1283-6. doi: 10.1002/anie.200805488.

Abstract

An extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6-dihydroxybenzoic acid is the key step in the synthesis of (-)-berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Hydroxybenzoates / chemical synthesis*
  • Spiro Compounds / chemical synthesis*
  • Stereoisomerism

Substances

  • Aldehydes
  • Hydroxybenzoates
  • Spiro Compounds
  • berkelic acid
  • gamma-resorcylic acid