1990 年 48 巻 8 号 p. 738-748
Nogalamycin (1) and its congeners are notable members of the anthracycline family because of their promising antitumor activity. Especially, 7-con-O-methylnogarol (2), the semisynthetic derivative of 1, has been selected for clinical trials. This review deals with the first total synthesis of the nogalamycin congeners, (+) - nogarene (3), (+) -7-deoxynogarol (4), (+) -2, and their related compounds. This synthesis involved the stereocontrolled synthesis of the naphthoquinone (44), the CDEF-ring system, and regioselective Diels-Alder reaction of 44 with highly functionalized dienes. Antitumor activity assay of the artificial nogalamycin congeners disclosed novel aspects of the structure-activity relationships.