Cyclic peroxyacetal lactone, lactol and ether compounds

Details Cyclic peroxyacetal lactone, lactol and ether compounds Cyclic peroxyacetal lactone, lactol and ether compounds

1994-01-24

1995-05-30

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 12, 549 17, 549 31, 549349, 549361, C07D41100, C07D32300

Patent

active

054202990

ABSTRACT:
##STR1## A process for preparing a compound containing (a) peroxyacetal lactone, (b) peroxyacetal lactol or (c) peroxyacetal ether functionality comprising oxygenating in the presence of one or more oxidizing metal catalysts a compound containing (i) hydroperoxy alkene carboxylic acid, (ii) hydroperoxy alkene aldehyde, (iii) hydroperoxy alkene keto, (iv) hydroperoxy alkene alcohol functionality or (v) dialkyl acetals of compounds in (ii) and (iii) above. For example (I).fwdarw.(II) wherein n=1, 2 or 3; m=0, 1, or 2, p=0, 1, 2 or 3; R.sup.5 =--COOH, --C(O)R, --CROH, (.alpha.), where R is H, alkyl, aryl or arylalkyl; R.sup.1 are independently alkyl, arylalkyl or each R.sup.1 together with the group --O--C--O-- to which they are attached form a cyclic acetal; X=CR.sup.2 R.sup.3, O, S, SO, SO.sub.2 where R.sup.2 and R.sup.3 are independently selected from H, optionally substituted alkyl, optionally substituted aryl, and wherein when n>1, X is independently selected and can be branched or straight chain and X together with a substituent Y can also form a ring; Y is a substituent selected from H; optionally substituted alkyl or aryl; Y can be on the same C atom as the hydroperoxy group and any C atom may be disubstituted by Y and includes replacement of H atom(s) in "(CH.sub.2).sub.m " by Y; R.sup.6 or R.sup.7 is as defined for R above, H, OH, OR.sup.1 or together with the carbon atom to which they are attached form a keto group. The present invention is particularly important in its application to the preparation of biologically active compounds comprising the cyclic peroxyacetal lactone or lactol functionalities. One such biologically active compound is qinghaosu (Artemisinin)

REFERENCES:
patent: 4992561 (1991-02-01), Roth et al.
"A Short and Stereospecific Synthesis of (+)-Deoxoartemisinin and (-)-Deoxodesoxyartemisinin," Jung et al., Tetrahedron Ltrs., vol. 30, pp. 5973-5976, 1989.
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"A Concise and Stereoselective Synthesis of (+)-12-n-Butyldeoxartemisinin," Jung et al., Synlett, 1990, pp. 743-744.
"The Development of New Peroxidic Antimalarials," Haynes et al., Chemistry in Australia, Mar. 1991, pp. 66-67.
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"Practical Conversion of Artemisinic Acid into Deoxyartemisinin," Jung et al., J. Org. Chem., 1986, 51, No. 26, 1985, pp. 5417-5419.
"Total DSynthesis of Arteanuuin (Quinghaosu) and Related Compunds," Zhou, Pure and Applied Chemistry, 58, No. 5, 1986, pp. 817-824.

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