95778-57-7Relevant articles and documents
The Synthesis of 9-Substituted p-Mentha-1,8(10)-diene Derivatives
Suemune, Hiroshi,Iwasaki, Genji,Ueno, Kohshi,Sakai, Kiyoshi
, p. 4632 - 4636 (2007/10/02)
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 1-2h 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.Keywords - synthesis; lithiation; limonene; perillyl alcohol; electrophile