Synthesis of the potent antiviral oxetane nucleoside epinoroxetanocin from D-lyxonolactone

Wang Y, Fleet GWJ, Storer R, Myers PL, Wallis CJ, Doherty O, Watkin DJ, Vogt K, Witty DR, Wilson FX, Peach JM

A short synthesis of epinoroxetanocin [9-(β-D-threo-oxetanosyl)adenine], free from its α-anomer, from D-lyxonolactone is described. The X-ray crystal structure of a benzylidene-protected derivative of epinoroxetanocin is reported. A comparison of the in vitro activity against HIV-1 of oxetanocin, noroxetanocin and epinoroxetanocin as anti-viral agents is given. © 1990.