Revision and confirmation of the regiochemistry of isoxazoles derived from methyl oleanonate and lanost-8-en-3-one. Synthesis of a new lanostane triterpenoid with a cyano-enone functionality in ring A

J Org Chem. 2003 Jun 13;68(12):4991-3. doi: 10.1021/jo034056y.

Abstract

It was previously reported that methyl oleanonate (5) and lanost-8-en-3-one (10) give predominantly [3,2-c]isoxazoles. On the contrary, we have confirmed that both compounds 5 and 10 do not give [3,2-c]isoxazoles but rather afford regioselectively [2,3-d]isoxazoles in good yields. Consequently, a new lanostane triterpenoid with a cyano-enone functionality in ring A was synthesized in two steps from the corresponding [2,3-d]isoxazole, which is interesting from the perspective of biological activity because lanosterol is the biogenetic precursor of steroids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Isoxazoles / analysis
  • Isoxazoles / chemistry*
  • Lanosterol / chemical synthesis*
  • Lanosterol / chemistry*
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry*
  • Stereoisomerism
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry*

Substances

  • Isoxazoles
  • Triterpenes
  • Lanosterol
  • Oleanolic Acid