17098-71-4Relevant academic research and scientific papers
First synthesis of Xerulin, an inhibitor of the biosynthesis of cholesterol
Siegel, Konrad,Brückner, Reinhard
, p. 1227 - 1230 (2007/10/03)
Starting from L-ascorbic acid, crotonaldehyde, (trimethylsilyl)acetylene and the stannylated alcohol 15, the title compound 4 was synthesized for the first time. L-Ascorbic acid was elaborated into phosphonium bromide 19 with a high degree of Z-stereoselectivity while the other starting materials were combined for obtaining the unsaturated aldehyde 5. A Wittig reaction between this aldehyde and the ylide derived from bromide 19 provided xerulin (4) along with a mixture of isomers which was readily separable.
