Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. (S)-2-Me-CBS-catalysed reduction of alnustone with BH3. SMe 2 gave (R) (-)(4E,6E)-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na in t-BuOH at –15 °C under NH3 atm gave (E)-1,7-diphenylhept-5- en-3-one as a Birch-type reduction product. t-BuOK catalysed condensation of benzalacetone with propionyl chloride gave (4Z,6E)-5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. (1E,4Z,6E)-5-Hydroxy-4-phenethyl1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. |
