Synthesis of phenolic components of Grains of Paradise

Abstract Two vanilloids, (5 E )-8-(4-hydroxy-3-methoxyphenyl)oct-5-en-4-one ( 1 ) and 4-[3-hydroxydecyl]-2-methoxyphenol ( 2 ), isolated from the dried seeds of Grains of Paradise ( Aframomum melegueta ), were synthesized; the latter compound was made as the S -enantiomer and the material derived from the seeds was found to be a 1:1.7 mixture of the R and S isomers. The synthetic route used should allow the preparation of analogs having extended alkyl chains and consequently different lipophilicity, and 3 , a homolog of 2 , was also prepared.