The Synthesis of Royal Jelly Acid and Its Homologs from Cycloalkanones1

EE Smissman, JF Muren, NA Dahle

Index: Smissman,E.E. et al. Journal of Organic Chemistry, 1964 , vol. 29, p. 3517 - 3520

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Citation Number: 15

Abstract

Two methods for the synthesis of royal jelly acid, trans-10-hydroxy-2-decenoic acid (Ia), from cyclooctanone are reported. Homologs of Ia were prepared utilizing one of the methods which involved an initial oxidation of a cycloalkanone to an o-lactone (11). The resulting lactone was treated with sodioacetonitrile to produce a 3-keto-w-hydroxynitrile (IX), which was reduced and hydrolyzed to afford the corresponding 3, wdihydroxycarboxylic acid ( ...