Turkish Journal of Chemistry, Vol.27, No.1, 31-34, 2003
An efficient synthesis of alnustone, a naturally occurring compound
Alnustone, 4(E),6(E)-1,7-diphenyl-hepta-4,6-dien-3-one, was synthesized starting from benzaldehyde in three steps with an overall yield of 57%. The condensation of benzaldehyde with acetone gave benzalacetone. The Pd-C catalyzed hydrogenation of benzalacetone afforded benzylacetone. The in situ enamination of benzylacetone with pyrrolidine and acetic acid followed by cinnamaldehyde treatment gave alnustone.
Keywords:alnustone;4(E),6(E)-1,7-diphenyl-hepta-4,6-dien-3-one;diarylheptanoid;benzaldehyde;benzalacetone;benzylacetone;cinnamaldehyde