Convergent approach to complex spirocyclic pyrans: practical synthesis of the oxa-pinnaic acid core

Org Biomol Chem. 2013 Jun 7;11(21):3469-76. doi: 10.1039/c3ob40284c. Epub 2013 Apr 16.

Abstract

The enantioselective synthesis of the oxa-pinnaic acid framework has been achieved through internal asymmetric induction. The synthetic strategy pursued illustrates the adaptability of the Achmatowicz oxidative rearrangement for the synthesis of complex spirocyclic pyrans starting from tertiary alcohols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry*
  • Pyrans / pharmacology
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Spiro Compounds / pharmacology

Substances

  • Alkaloids
  • Pyrans
  • Spiro Compounds
  • pinnaic acid