A rapid divergent synthesis of highly substituted delta-lactones

Org Lett. 2006 Oct 12;8(21):4779-82. doi: 10.1021/ol0617695.

Abstract

[reaction: see text] Nucleophilic 1,2-addition of (Z)-gamma-silyloxyvinylzinc reagents to ethyl glyoxylate followed by desilylation and cyclization affords 3,6-dihydro-3-hydroxypyran-2-ones in good chemical yields. In situ formation of allylic phosphates followed by reaction with RCu(CN)Li reagents affords substituted 5,6-dihydropyran-2-ones. The parent compound, 3,6-dihydro-3-hydroxypyran-2-one, undergoes allylic phosphate formation, cuprate-mediated allylic substitution, and 1,4-conjugate addition to afford trans-4,5-disubstituted tetrahydropyran-2-ones in a one-pot process.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Cyclization
  • Lactones / chemical synthesis*
  • Lactones / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism

Substances

  • Lactones
  • Organometallic Compounds
  • Pyrones