Total synthesis of a novel benz[A]anthracycline analog of the antitumor agent 4-demethoxydaunorubicin

Bioorganic & Medicinal Chemistry Letters
1994.0

Abstract

The total synthesis of 2s. 4S-2-acetyl-4-[(3-amno-2,3,6-trideoxy-a-1,2,3,4-tetrahydro-2.5.6-trihydroxy-benz[a]~th~cene-?,lZdione (5) and its 2R. 4Rdiastereomer (23) was accomplished in 11 steps (1.4% overall yield) from 5.6Qmethoxy-Ztetralone (8). These angular analogs of 4 demethoxydaunorubicin were inactive in tissue culture assays in comparison with doxorubicin.

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