SELECTIVE PROTECTION OF THE PRIMARY HYDROXYL GROUPS OF OXETANOCIN A AND CONFORMATIONAL ANALYSIS OF O-PROTECTED OXETANOCIN A

Abstract

One of the two primary hydroxyl groups of oxetanocin A was protected selectively with acetyl and o-nitrobenzyl groups using enzymatic and photochemical reactions, respectively. On the basis of ¹H-NMR spectroscopy and NOE experiment, 4'-O-protected oxetanocin A was found to take syn conformation in an aprotic solvent irrespective of the kind of protecting group owing to an intramolecular hydrogen bond.