Synthesis of anthracyclines
AssigneeResearch Corporation
InventorsFrancis Johnson, Kyoung S. Kim
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Abstract
There is provided a novel method of synthesizing certain heterocyclic quinones. In particular there is provided a novel and regiospecific synthesis of 9-acetyl-6,11-dihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-quin one (7,9-dideoxydaunomycinone) which is known intermediate in the synthesis of daunomycinone. There is also provided a method of preparing analogs of 7,9-dideoxydaunomycinone which thus provide for the preparation of known and desired analogs of daunomycinone. Daunomycinone is a known compound which is an intermediate in the preparation of the clinically accepted naturally-occurring antitumor antibiotics daunomycin and its derivitive adriamycin.
Claims2
A compound of the formula ##STR1## and the enol forms thereof wherein R.sub.1,R.sub.2, R.sub.3, and R.sub.4 may also be the same or different and are each selected from the group consisting of hydrogen, alkyl, alkoxy, and halo, R.sub.5 is alkyl wherein the alkyl and alkoxy moieties contain 1-5 carbon atoms, Z is
- --CR.sub.13 H.C(COOR.sub.15).sub.2 (CH.sub.2).sub.2 --
- wherein the bondings indicated at both terminals of the Z group indicate position on the ring of the principal formula, but not stereo chemical orientation, R.sub.13 is alkyl of 1-5 carbon atoms or hydrogen, R.sub.15 is lower alkyl of 2-6 carbon atoms.
Dependencies are inferred from the claim text.