Cyclic peroxyacetal lactone and ether compounds

Details Cyclic peroxyacetal lactone and ether compounds Cyclic peroxyacetal lactone and ether compounds

C - Chemistry, Metallurgy

07

D

C07D 493/18 (2006.01) C07D 321/10 (2006.01) C07D 409/14 (2006.01) C07D 493/20 (2006.01) C07D 497/18 (2006.01)

Patent

CA 2067101

2067101 9104970 PCTABS00003 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) $m(8) (II) wherein n = 1, 2 or 3; m = 0, 1, 2, 3 or 4; p = 0, 1, 2 or 3; R5 = -COOH, -C(O)R, -CROH, (.alpha.), where R is H, alkyl, aryl or arylalkyl; R1 are independently alkyl, arylalkyl or each R1 together with the group -O-C-O- to which they are attached form a cyclic acetal; X = CR2R3, O, S, SO, SO2 where R2 and R3 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 "(CH2)m" by Y; R7 or R8 is as defined for R above, H, OH, OR1 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).

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