Dispiro-l,2,4,5-tetraoxanes

Treatment of variously substituted cyclohexanones with H2O2 in acidic medium leads to formation of dispiro-l,2,4,5-tetraoxanes (16, Section II.A.2.a). The products obtained in the case of 16a and 16b are mixtures of the meso, D- and L-stereoisomers, whereas 16c is a single compound. See also Scheme 7 for the formation of cis- and trans-3,6-dichloro-l,2,4,5-tetraoxanes, obtained on ozonolysis of 1,2-dichloroethylene " . 

Dispiro-l,2,4,5-tetraoxanes (45 1-3) were prepared with the intact peroxide functional group and tested for antimalarial activity [51], Dispiro-1,2,4,5-tetraoxanes, 1(5), 10( )-dimethyl-7,8,15,16-tetraoxodispiro[5,2,5,2]hexadecane (45 3) was as active as artemisinin, both in vitro and in vivo. Based on the resistance index (IC50(W-2)/IC5o(D-6)), 2,4,1 l,13-tetramethyl-7,8,15,16 tetraoxodispiro[5,2,5,2]hexadecane... 

Dong, Y McCullough, K.J., Wittlin, S Chollet, J., and Veimerstrom, J.L. (2010) The structure and antimalarial activity of dispiro-l,2,4,5-tetraoxanes derived from (-l-)-dihydrocarvone. Bioorg. Med. Chem. Lett., 20, 6359-6361. 

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