The hydrochloride of (-)-(8R)-8-acetyl-7,8,9,10-tetrahydro-6,8-dihydroxy-11-[(3'aminopropyloxy)methyl]naphthacene-5,12-dione was derived from 1-(dimethoxymethyl)-2,3,5,6--tetramethylidene-7-oxabicyclo[2.2.2]heptane and shown to be a moderate intercalator of calf thymus DNA type XV.Adriamycin (1) and daunomycin (2) are the most valuable anticancer drugs in present clinical use.1 Their effectiveness however, is restricted due to accute bone marrow toxicity and cardiotoxicity.2 Since the cytotoxic mechanism by which these drugs act is still unclear,3 the influence of structural alteration on activity remains an important issue.4a For instance, the 4-demethoxy derivatives 3 and 4 exhibit improved pharmaceutical profiles.4b We report here the synthesis of the anthracycline analogue (-)-5 obtained in a highly enantioselective fashion. Compound (-)-5 is the first member of a new class of anthracyclinones Csubstituted at C(6) with a(3-aminopropyloxy)methyl group that may imitate the L-daunosaminyl unit in 1-4.5 Furthermore, the benzylic system at C(6) might compensate the lack of a benzylic nucleofugal group at C(7) .6 Preliminary assays have shown compound (-)-5 to intercalate into calf thymus DNA and to inhibit topoisomerase I induced relaxation of circular plasmids.