Chemical transformation of abietic acid to new chiral derivatives

Abstract

Chemical transformations of the C-ring abietic acid (1a) for the preparation of some new chiral synthons are described. From the intermediate keto-aldehyde 9, readily available from 1b through the ozonide 2, the new tetracyclic diterpene 4 was synthesized. Additionally, from 13 and 17, previously prepared from 2, the bicyclic compounds 14, 15 and 16 and the derivatives containing the abeo-abietane[6,6,5] framework 19 and 20 were also synthesized.

Keywords

• abietic acid
• ozonization
• chiral synthon
• abeo-abietane derivatives