The synthesis of 6-deoxyanthracyclinones: (±)α-citromycinone and (±)4-demethoxy-6-deoxydaunomycinone

Add time:07/29/2019    Source:sciencedirect.com

Two synthetic approaches have been explored to prepare 6-deoxyanthracyclinones in general and α-citromycinone in particular. The first approach employed as starting materials 1,4,5-trimethoxynaphthalene and the Diels-Alder product from butadie regioselective carbon acylation of 4-hydroxy-l,5-dimethoxynaphthalene with the half-ester acid chloride of cis-4,5-dicarboxycyclohexene. The resulting product was converted to 7,10-dideoxy-α-citromycinone; however, even the C-7—OH group required for glycosylation could not be introduced satisfactorily into this product. The second strategy employed as the key step the coupling of a highly functionalized metallated quinol equivalent with the monoketal of a benzocyclobutenedione. This route gave (± )-α-citromycinone and (±)-4-demethoxy-6-deoxydaunomycinone in quantities suitable for biological testing.

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