A divergent chemoenzymatic route to an intermediate for nucleoside analogues

Two regioisomeric isoxazoline monoacetates 1 and 2 were synthesized from the corresponding diacetate 3 via PPL or PLE catalyzed hydrolysis. With both the enzymes, the initial regioselectivity ( 3–4:1) was offset by an intramolecular acyl transfer. In addition to a non-enzymatic catalysis for the acyl transfer, preliminary experiments do suggest a definite but minor role of enzyme for this intramolecular acyl transfer. Compounds 1 and 2 may serve as intermediates for nucleoside analogues.