合成路线1

The chiral aldehyde (XI) can also be obtained as follows: The reaction of dodecanal (XXV) with allylmagnesium bromide (XXVI) in THF gives 1-pentadecen-4-ol (XXVII) as a racemic mixture, which is esterified with 2(R)-acetoxy-2-phenylacetic acid (XXVIII) by means of dicyclohexylcarbodiimide (DCC) and dimethylaminopyridine (DMAP) to yield the diastereoisomeric mixture of esters (XXIX) and (XXX), which are separated by flash chromatography. The hydrolysis of (XXIX) and (XXX) with KOH in methanol affords the alcohols (XXXI) and (XXXII). The unwanted isomer (XXXII) can be isomerized to (XXXI) through the formation of the 4-nitrobenzoyl ester and hydrolysis with K2CO3. The benzylation of (XXXI) with benzyl bromide and KH in THF gives the benzyl ether (XXXIII), which is finally ozonolyzed to the desired aldehyde (XI) with O3 in methanol-dichloromethane.