Plakinic acids

In addition to these extensive studies on electrophile-mediated intramolecular peroxydation of electron-rich C=C bonds, some examples of intramolecular hydroperoxide addition to electron-poor C=C bonds have been described. For example, several racemic analogues 371 of the naturally occurring plakinic acid were readily obtained by peroxymercuration followed by hydridodemercuration of the dienic acids 370 (Scheme 95 f °. Intramolecular Michael addition of hydroperoxide function to the double... 

Triethysilyl-protected peroxycarbenium ions (42), generated from acetals (41) on treatment with SnCL, have been developed as the optimal reagents to effect addition to alkenes, which gives rise to a variety of 1,2-dioxolanes (43) in 28-92% yields. This novel method allowed the synthesis of plakinic acid analogues in three steps from the corresponding ketone and alkene.53... 

Dalisay, D.S., Quach, T, Nicholas, G.N., and Molinski, T.F. (2009b) Amplification of the Cotton effect of a single chromophore through liposomal ordering-stereochemical assignment of plakinic acids I and J. Angew. Chem. Int. Ed., 48, 4367-4371. 

Bloodworth, A.J., Bothwell, B.D., Collins, A.N., and MaidweU, N.L. (1996) A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group. Tetrahedron Lett., 37,1885-1888. 

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