Abstract
AbstractLead tetraacetate (LTA) oxidation of the allylic alcohols 1, 10, 14 and 19 leads to the formation of the epoxides 2, 11, 15 and 20, products of a novel internal addition reaction of the electron deficient alcohol oxygen to the allylic double bond. In some cases (10, 14) the formation of a new type of acetoxylated enolethers (12, 16) is observed. The LTA oxidation of the allylic dienols 21 and 29 gives rise to the formation of the epoxyacetates 25 and 33, products of a similar internal addition reaction. Furthermore, a variety of cyclization products (22, 23, 24, 26, 30, 31, 32 and 34) has been isolated whose formation requires an isomerisation of the allylic trans double bond to a cis one.
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