RADIOISOTOPES
Online ISSN : 1884-4111
Print ISSN : 0033-8303
ISSN-L : 0033-8303
14C-Labeling of a Novel 9-Aminoanthracycline
Kazuhiko NISHIOKAKeiichi FUJIMOTOHiroshi KANAMARU
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1996 Volume 45 Issue 6 Pages 353-359

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Abstract

(+) -9-Amino-4-demethoxy-9-deoxy-7-O- (2-deoxy-β-D-erythro-pentopyranosyl) daunomycinone (1a) was labeled with carbon-14 for use in mammalian metabolic studies. The synthesis was achieved according to the scheme illustrated in Fig. 3. Friedel-Crafts acylation of [carbonyl-14C] phthaloyl chloride (2) with the optically active bicyclic amidoketone (3) gave the tetracycline amidoketone (4) . Protection of the C13-carbonyl group of 4 with neopentylglycol furnished the ketal (5) . Treatment of 5 with 1, 3-dibromo-5, 5-dimethylhydantoin under illumination produced the oxazine (6) . Hydrolysis of the oxazine ring of 6 under acidic condition and subsequent deketalization afforded the aminoketone (8) . Glycosidation of 8 with acetyl 2-deoxy-3, 4-di-O-acetyl-D-erythro-pentopyranose in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) provided the acetylated glycoside (10) . Alkaline hydrolysis of 10 with potassium bicarbonate gave la. The overall yield was 12.4% from 2.

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© Japan Radioisotope Association
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