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Synthetic approaches to new anthracyclines: 4,11-dideoxy-2-hydroxy-β-rhodomycinone and its glycosides

✍ Scribed by Hiroshi Tanaka; Takeo Yoshioka; Yasutaka Shimauchi; Akihiro Yoshimoto; Tomoyuki Ishikura; Hiroshi Naganawa; Tomio Takeuchi; Hamao Umezawa


Book ID
104233750
Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
215 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis


f)-Z-Acetoxy-4,ll-dideoxy-lO-oxo-B-rhodomycinone [(+)-621 was synthesized from the tricyclic quinone ((l_) by a short efficient route in an overall yield of about 54%. Reaction of (!)-@ with protected daunosamine followed by reduction and deprotection provided the optically active o-glycosidated anthracycline (II) with the 7S,9R,lOR-configuration.

Furthermore, the amino and aromatic hydroxy gro%s Of ,II_ were methylated.