Acid-catalyzed reactions of epoxides derived from citronellene
作者:T. M. Khomenko、D. V. Korchagina、V. A. Barkhash
DOI:10.1007/s11178-005-0035-z
日期:2004.10
Transformations of epoxy derivatives of citronellene in the presence of acid catalysts (ZrO2/SO 4 2− , SnCl4, H2SO4) in methylene chloride, acetone, and acetonitrile give rise to various oxygen- and nitrogen-containing compounds.
A seven-step synthesis of S-(+)-hydroprene (S-1) in similar to 20% overall yield starting from S-(+)-3,7-dimethyl-1,6-octadiene (2) of 55+/-10% optical purity is described. The introduction of an optical enhancement step in the synthetic sequence at the stage of S-(-)-3,7-dimethyl-1-octanol (9) raises the optical purity of S-1 from similar to 50% to similar to 80%.
A Stereocontrolled Access to (±)-, (−)-, and (+)-Patchouli Alcohol
The racemate and both enantiomers of patchouli alcohol have been synthesized by stereocontrolled routes. The olfactive properties of the patchouli alcohols prepared are reported.