Synthesis of a Functionalized 7,6-bicyclic Spiroimine Ring Fragment of the Spirolides

Org Lett. 2010 Nov 19;12(22):5226-9. doi: 10.1021/ol102525w. Epub 2010 Oct 28.

Abstract

The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Molecular Conformation
  • Molecular Structure
  • Shellfish Poisoning
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Spiro Compounds
  • spirolide A