A new synthetic approach towards adriamycin

Abstract

An improved route to 3,4-dihydro-2-phenylnaphtho[1,8-b,c]furan-5-one (2) and a convenient preparation of furan-3,4-dicarbaldehyde (4) are described. The dihydro-derivative of (2) was condensed with (4) to give 4-(4-formyl-3-furylmethyl)-2-phenylnaphtho[1,8-b,c]furan-5-one (5), which after preparation of its 1,3 dithiolan derivative was photocyclised to a polycyclic compound (7). Owing to problems of deprotection of (7) further steps towards adriamycin (1) were abandoned.