The anthracycline antibiotics adriamycin(3 and daunorubicin(8 are of current interest because of their activity against various experimental tumors as well as certain types of human cancer.') Studies on the structure-activity relationship have revealed that 4-demethoxy analogues of !, and g show improved therapeutic properties. 132) Although various syntheses of the anthracyclinones, aglycones of the anthracyclines, have been reported in racemic modifications, 3-B) seem quite limited, 9) efficient methods to produce optically active anthracyclinones and no attempts have been made in the area of their asymmetric syntheses Recently the asynzaetric bromolactonization reaction was developed as an effective method J: X=OH 2: X-H N H for converting a,6-unsaturated acid into highly optical. ly active a-hydroxy acid. 12) Applicability of this novel asytnnetric reaction to the preparation of optical. ly active anthracyclinones has already been proven to be quite promising by the model study. 13) Based on these results, asynzsetric synthesis of optically active anthracyclinones is attempted using two different types of a,$-unsaturated acids($&) which possess AB and ABC0 ring systems of anthracyclinones, as reaction substrates. Two types of a,B-unsaturated acids(s) were prepared from 1,4-dimethoxybenzene($ following the reaction scheme shown in Scheme-I. ide14) followed by Clemmensen reduction 15) Thus, acylation of iwith succinic anhydraccording to the reported procedure, 14,15) afforded the known acid(3, mp 60-62"C(lit., 15a) mp 64.5-67ยฐC; lit., 15b) mp 61-62"C), which on esterification(conc. H2S04-EtOH) gave the ethyl ester(k)16a)(63%). bp 155-158'C(3 mnHg).