Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive‐Pressing Residues

Abstract

Maslinic acid, a naturally occurring compound isolated from the solid wastes of olive‐oil pressing, was fragmented through the C‐ring via oxidative procedures to obtain two structural fragments. The chemical behaviors of cis‐decalin, from the D and E rings, and of trans‐decalin fragments, from the A and B rings, were investigated in depth using several chemical and enzymatic reactions. These decalin chiral synthons are interesting intermediates to semisynthesize phenanthrene‐ and drimane‐type compounds and natural tricyclic triterpenes.

Keywords:

• Maslinic acid
• oleanene
• olive oil
• oxidative cleavage
• sesquiterpe synthons
• triterpene

Acknowledgments

This work was supported by a project from the Ministerio de Educación y Cultura (PM98‐0213) and from the Ministerio de Ciencia y Tecnología (PPQ2002/01331). We thank our colleague A. L. Tate for revising the English of our text.