Total synthesis of pyranicin

Org Lett. 2005 Jan 20;7(2):199-202. doi: 10.1021/ol0479242.

Abstract

[Reaction: see text] A stereocontrolled convergent synthesis of the annonaceous acetogenin pyranicin (1) is presented. Asymmetric Horner-Wadsworth-Emmons (HWE) reactions were used to access key intermediates. The tetrahydropyran derivative 2 was obtained via an asymmetric desymmetrization of the meso-dialdehyde 6, and the butenolide fragment was constructed using a stereoconvergent reaction sequence involving a parallel kinetic HWE resolution followed by a Pd-catalyzed allylic substitution. The C10/C15 1,6-diol motif was installed using Carreira's asymmetric acetylide addition methodology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Furans / chemical synthesis*
  • Lactones / chemical synthesis*
  • Molecular Structure
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Furans
  • Lactones
  • pyranicin
  • Palladium