合成路线1

The aminoacid building block (VIII) can be prepared by two different ways. The oxidative cleavage of 7-octene-1,2-diol (I) by means of NaIO4 yields aldehyde (II). Partial hydrolysis of diethyl 2-acetamidomalonate (III) provides monoacid (IV), which is subjected to Knoevenagel-type condensation with 6-heptenal (II) in the presence of Ac2O and pyridine to afford enamide (V). Enantioselective hydrogenation of the enamide double bond to the (S)-amidoester (VI) is then achieved by using the Burk's method. In order to replace the N-acetyl protecting group of (VI), the acetamide nitrogen is protected with Boc2O, and the resulting imide (VII) is further hydrolyzed to the target N-Boc aminoacid (VIII) under standard basic conditions.