| Abstract
| - A rapid Diels−Alder approach to halogenated biaryl templates is described. These biaryl templates areavailable in two steps from the corresponding aromatic aldehydes. The scope of subsequent Suzukicouplings on the biaryl chlorides is explored. Good tolerance for both electron-donating and electron-withdrawing groups in the coupling process can be achieved. Further functionalization of the biaryltemplates is described. Hydrogenation of the nitro moiety with concomitant removal of the benzyl etheryields the o-anilino, o-phenolic polyaryls. Selective reduction of the nitro group can be accomplished.Alternatively, the benzyl ether can be selectively removed under Lewis acidic conditions. The utilizationof the Diels−Alder adducts for the synthesis of a series of chlorinated carbazoles via the Cadogancyclization is also demonstrated. Finally, application of this technology to the total synthesis of siamenol,an anti-HIV agent, is reported.
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