Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor
The Journal of Organic Chemistry1997Vol. 62(11), pp. 3440–3448
Citations Over TimeTop 12% of 1997 papers
Pierre L. Beaulieu, Pierre Lavallée, Abraham, Paul C. Anderson, Colette Boucher, Yves Bousquet, Jean‐Simon Duceppe, James Gillard, Vida Gorys, Chantal Grand‐Maître, Louis Grenier, Yvan Guindon, Ingrid Guse, Louis Plamondon, François Soucy, Serge Valois, Dominik Wernic, Christiane Yoakim
Abstract
Palinavir is a potent peptidomimetic-based HIV protease inhibitor. We have developed a highly convergent and stereoselective synthesis which is amenable to the preparation of multikilogram quantities of this compound. The synthetic sequence proceeds in 24 distinct chemical steps (with several integrated, multistep operations) from commercially available starting materials. No chromatographies are required throughout the process, and the final product is purified by crystallization of its dihydrochloride salt to >99% homogeneity.
Related Papers
- → Efficient parallel synthesis of macrocyclic peptidomimetics(2008)35 cited
- → Design and Synthesis of New PotentC2-Symmetric HIV-1 Protease Inhibitors. Use ofl-Mannaric Acid as a Peptidomimetic Scaffold(1998)77 cited
- → HIV-1 Protease Inhibitors: A Comparative QSAR Analysis(2003)39 cited
- → Diversity‐Oriented Synthesis of Diol‐Based Peptidomimetics as Potential HIV Protease Inhibitors and Antitumor Agents(2018)4 cited
- → Acute thrombocytopenia secondary to the administration of the peptidomimetic HIV protease inhibitor MK-639 (L735524)(1996)21 cited