SYNTHESIS OF THE CARBOCYCLIC ANALOGUE OF OXETANOCIN A

Abstract

2, 3-Bis(benzoyloxymethyl)cyclobutanone (3__∼) was prepared in three steps from diethyl 3, 3-diethoxy-1, 2-cyclobutanedicarboxylate (1__∼). Hydrogenation of the oxime (4__∼) of 3__∼ provided the two amino compounds ((5a)___∼ and (5b)___∼), from which 9-[2, 3-bis(hydroxymethyl)cyclobuthyl]adenines ((9a)___∼ and (9b)___∼) were synthesized in four steps. The steric configurations of 3__∼, (5a)___∼, (5b)___∼, (9a)___∼ and (9b)___∼ were established by ¹H-NMR spectroscopies including the NOE difference experiments.