Synthetic Anthracyclines : Total Synthesis of D-Ring Pyridine and Pyrazine Analogues of 11-Deoxydaunomycin

• Published in: Chemical & pharmaceutical bulletin Vol. 39; no. 4; pp. 857 - 864
• Main Authors: KITA, Yasuyuki, SHIMOOKA, Kin-o, MAEDA, Hiroshi, ISHIDA, Toshimasa, AKAI, Shuji, FUJII, Yuji, OHISHI, Hirofumi, OKUNAKA, Ryuichi, TAMURA, Yasumitsu, KIRIHARA, Masayuki
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 25.04.1991; 公益社団法人日本薬学会; Maruzen
• Subjects: 11-deoxydaunomycin analogue; antitumor agent; azatetrahydronaphthacene; Chemistry; Condensed matter: structure, mechanical and thermal properties; cycloaddition; Exact sciences and technology; heteroanthracycline; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Organic compounds; Physics; Preparations and properties; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Antineoplastic agent; Molecular structure; Nitrogen heterocycle; Quinone; Tetracyclic compound; Experimental study; X ray diffraction; Spiran; Acetal; Cycloaddition; Aromatic compound; Organic compounds; Crystalline structure
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.39.857

Treatment of sodium salts generated from tetrahydrohomophthalic anhydrides (6a, b) with 5, 8-dihydro-5, 8-dioxoquinoline (9) gave cycloadducts (7 and 8), regioselectively. These adducts were converted to the D-ring pyridine analogue (21) of 11-deoxydaunomycin. The D-ring pyrazine analogue (27) of 11-deoxydaunomycin was also prepared by a similar method.