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The reduction of (3S)-N,N-dibenzylamino-2-ketophosphonate 5 derived from L-leucine with catecholborane at -20 o C afford the (3S)-N,N-dibenzylamino-(2R)-hydroxyphosphonate syn-6, whereas the reduction of (3S)-N-benzylamino-2-ketophosphonate 9 with Zn(BH4)2 at -78 o C gave the (3S)-N-benzylamino-(2S)-hydroxyphosphonate anti-10. The reduction in both cases was in good chemical yields and high diastereoselectivity. The hydrolysis and hydrogenolysis of syn-6 and anti-10 gave phosphostatine 12 and phosphoepistatine 13, respectively.

Preparation of phosphostatine and phosphoepistatine from L-leucine via high diastereoselective reduction of 3-amino-2-ketophosphonates