An Efficient Synthesis of Alnustone, a Naturally Occurring Compound

Authors: SÜLEYMAN GÖKSU, HÜLYA ÇELİK, HASAN SEÇEN

Abstract: 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

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