An easy route to 11-hydroxy-eudesmanolides. Synthesis of (±) decipienin A

Article abstract of DOI:10.1016/S0040-4020(99)00328-2

The preparation of 11-hydroxy-eudesmanolides with the stereochemistry found in the Umbelliferae family of plants is described. The decalin system of the eudesmane skeleton is produced by the addition of 5-methyl-2- furyllithium to 3-ethoxycyclohex-2-enone and acidic treatment of the resulting adduct. The stereochemistry of the decalones obtained by this method has been corrected. The α-hydroxy-γ-lactone moiety is obtained by condensation of the appropriate decalone with methyl pyruvate and subsequent reduction under Luche conditions. The usefulness of this procedure has been proven in the synthesis of decipienin A.