The Synthesis of 9-Substituted p-Mentha-1, 8 (10)-diene Derivatives

抄録

The chemical conversion of (+)-limonene (1) and (-)-perillyl alcohol (10) into 9-substituted p-mentha-1, 8 (10)-diene derivatives is described. The lithiated species of 1 and 10 were easily obtained in good yields, by using sec-butyl lithium in N, N, N', N'-tetramethylethylenediamine. The reaction of the lithiated species (A and B) with various electrophiles was completed within 1-2 h to give 9-substituted p-mentha-1, 8 (10)-diene derivatives. The stereochemistry of the chiral center of the starting material was retained in the products. 9-Hydroxy-p-mentha-1, 8 (10)-diene (8) was also obtained by another short sequence of steps. Oxidation of the phenylthio derivative (7) gave the sulfoxide (9). Treatment of 9 with trimethyl phosphite afforded 8.