Method of preparing (+)-deoxoartemisinin and selected analogues

Details Method of preparing (+)-deoxoartemisinin and selected analogues Method of preparing (+)-deoxoartemisinin and selected analogues

1990-08-10

1993-07-06

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549348, C07D49118, C07D32500

Patent

active

052255620

ABSTRACT:
This invention is a new method for preparing compounds useful as antimalarial agents having the formula; ##STR1## wherein R is hydrogen, a linear, branched or cyclo lower alkyl group having 1 to 8 carbon atoms; aminoalkyl; branched aminoalkyl; hydroxyalkyl: alkylcarboxylate or alkylbenzoate groups having 1 to 5 carbon atoms in the alkyl chains; aryl; alkoxy-substituted aryl; heteroaryl; and pyridinium groups. The method comprises treating artemisinic acid with a methylating agent followed by a stereoselective reduction of the methylated compound, subjecting the reduced compound to a Grignard addition followed by chiral photoxidation with subsequent treatment with a cyclization agent.

REFERENCES:
patent: 4920147 (1990-04-01), McChesney et al.
Jung et al. "Synthesis and antimalarial activity of (+) deoxoartemisinin" J. Med. Chem. 1990 vol. 33 pp. 1516-1518.
Jung et al "A Short and Stereospecific Synthesis of . . . " Tetrahedron Letters, vol. 30 No. 44 pp. 5973-5976 (1989).
Bustas et al. "Stereospecific Synthesis of (+-homodeoxo-artemisinin" Heterocycles vol. 29 No. 12 pp. 2273-2277 (1989).

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