Application of the chloro ketal Claisen reaction to the total synthesis of squalene.
A short, highly stereoselective (over 97%) synthesis of all-trans squalene is described. Starting with succinaldehyde, a tetraenedichlorodione having the complete squalene skeleton with the four internal trans olefinic bonds has been developed in four steps involving a sequence of two double Claisen rearrangements. Three simple operations convert this intermediate into squalene.
D008722:Methods; D013185:Squalene / Q000138:chemical synthesis*; D013237:Stereoisomerism
D013185:Squalene