- 著者
- 末宗 洋 岩崎 源司 上野 貢嗣 酒井 浄
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.32, no.11, pp.4632-4636, 1984-11-25 (Released:2008-03-31)
- 参考文献数
- 9
- 被引用文献数
- 2 5
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.