| Abstract: | The synthesis of the cyclopropyl silyl ketones 1 – 4 is described. The trimethylsilyl ketone 1 was prepared from geraniol ((E)- 5 ) in ca. 10% overall yield by cyclopropanation leading to 6 , CrO3 oxidation to the aldehyde 8 , reaction of the latter with trimethylsilyl anion to 14A + B , and CrO3 oxidation to 1 . Also for the (t-butyl)dimethylsilyl ketones 2 – 4 , an efficient four-step synthesis with overall yields of 48%, 85%, and 13%, respectively, was elaborated, starting from the allylic alcohols (E)- 5 , and 23 . The method of preparation involves as the key step a Wittig rearrangement of the silylallyl ethers ((E/Z)- 20 , 24 ) to the silyl alcohols ((E/Z)- 21 , 25 ), subsequent cyclopropanation ( 19A + B , 22A + B , 26 ), and oxidation to the cyclopropyl silyl ketones 2 – 4 . |
