Abstract
Treatment of methyl 12-(diethoxyphosphoryloxy)podocarpa-8,11,13-trien-19-oate (14)
or its 13-bromo derivative (7) with butyllithium
effects a rearrangement of the phosphate group to give methyl
13-diethoxyphosphoryl-12-hydroxypodocarpa-8,11,13-trien-19-oate (11) in high
yield. Similar treatment of some simple aryl phosphates indicates that the
rearrangement is general. The reaction, which probably occurs by means of an ortho-metallation-nucleophilic
displacement sequence, is superior to existing methods for the preparation of o-hydroxyaryl phosphonates.
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