118198-35-9Relevant academic research and scientific papers
Stereospecific Synthesis of Squalenoid Epoxide Vinyl Ethers as Inhibitors of 2,3-Oxidosqualene Cyclase
Ceruti, Maurizio,Viola, Franca,Dosio, Franco,Cattel, Luigi,Bouvier-Nave, Pierrette,Ugliengo, Piero
, p. 461 - 470 (2007/10/02)
The stereospecific synthesis of squalenoid epoxide vinyl ethers with an isopentyloxy group is described.The synthesis involves the preparation of the C22 squalenoid aldehyde bromohydrin (15) by a new method via a one-step cleavage of lipophilic epoxides using periodic acid in diethyl ether, and the preparation of (1-isopentyloxyethyl)diphenylphosphine oxide (24).The structure of this compound has been confirmed by X-ray analysis.The configuration of vinyl ethers, synthesized using a Wittig-Horner reaction, has been determined by (13)C n.m.r.Biological results show that vinyl ethers (5) and (27) are competitive inhibitors of 2,3-oxidosqualene cyclase from rat liver.
