SYNTHESIS AND CHEMISTRY OF QUINONE METHIDE MODELS FOR THE ANTHRACYCLINE ANTITUMOR ANTIBIOTICS

In an effort to further understand the chemistry of anthracycline-type quinone methides, two tetracyclic o-quinone methides, thylacetyl)oxy] -3-9,10-dihydro-6(2H)-naphthacenone (19) and ethylacetyl)oxy]-9,10-di- hydro-6(2H)-naphthacenone (20), were synthesized, and their reaction w ith several nucleophiles was investigated. Carbon-and sulfur-based nuc leophiles afforded stable adducts while oxygen-and nitrogen-based nucl eophiles afforded unstable adducts due to the reversibility of the add ition. Adducts of 19 with ethanol and O-silylated adenosine (27) were acetylated to afford stable phenol acetates 21 and 29, respectively.