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Synthetic Anthracyclinones, XXII. - Rhodomycinones of Type A with Methyl, Ethyl, and n-Propyl Side Chain
Krohn, Karsten,Behnke, Bert
, p. 1818 - 1838 (2007/10/02)
The anthraquinone derivatives 7, 8, 37, 39, and 40 are prepared by addition of dichloromethyllithium to the corresponding ketones 4, 5, 32b, 34b, and 36b.They can be hydrolized to intermediate aldehydes, which cyclize after reduction to anthracyclinones of Type A with methyl group (11, 12a, 13a, 45, 46a, 47a), ethyl group (15a, 16a, 48, 49, 50a), and n-propyl side chain (51a, 52a).The cis/trans ratio of the 7,8-Diols is approximately 1 : 3.The hydroxy groups at C-10 are introduced stereoselectively to the 8,10-cis-diols 20b, 24, 25a, 53, 54, and 55 via bromination and hydrolysis of the bromides.
