Substrate encapsulation: an efficient strategy for the RCM synthesis of unsaturated epsilon-lactones

Org Lett. 2008 Dec 18;10(24):5613-5. doi: 10.1021/ol8022227.

Abstract

A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

Publication types

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

MeSH terms

  • Furans / chemistry*
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Ruthenium / chemistry

Substances

  • Furans
  • Lactones
  • Ruthenium