Diels−Alder Approach for the Construction of Halogenated, o-Nitro Biaryl Templates and Application to the Total Synthesis of the Anti-HIV Agent Siamenol

Michael R Naffziger, Bradley O. Ashburn, Johanna R. Perkins, and Rich G. Carter*
Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, Oregon 97331
J. Org. Chem., 2007, 72 (26), pp 9857–9865
DOI: 10.1021/jo070740r
Publication Date (Web): June 29, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rich.carter@oregonstate.edu

Abstract

Abstract Image

A rapid Diels−Alder approach to halogenated biaryl templates is described. These biaryl templates are available in two steps from the corresponding aromatic aldehydes. The scope of subsequent Suzuki couplings 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 biaryl templates is described. Hydrogenation of the nitro moiety with concomitant removal of the benzyl ether yields 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 utilization of the Diels−Alder adducts for the synthesis of a series of chlorinated carbazoles via the Cadogan cyclization is also demonstrated. Finally, application of this technology to the total synthesis of siamenol, an anti-HIV agent, is reported.

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History

  • Published In Issue December 21, 2007
  • Received April 11, 2007

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