An efficient synthesis of the guaiane sesquiterpene (−)-isoguaiene by domino metathesis

Abstract

(−)-Isoguaiene was prepared from (S)-citronellal in only 9–10 steps with good overall yields. Either a trienyne or a dienediyne metathesis and highly diastereoselective organocatalytic Michael additions of aldehydes derived from (S)-citronellal served as the key transformations.

Keywords

• domino reactions
• metathesis
• Michael addition
• organocatalysis
• terpenes