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Ghosh AK, Xu CX, Osswald HL. Enantioselective Synthesis of Dioxatriquinane Structural Motifs for HIV-1 Protease Inhibitors Using a Cascade Radical Cyclization. Tetrahedron Lett. 2015;56(23):3314-3317doi: 10.1016/j.tetlet.2015.01.019.
Ghosh, A. K., Xu, C. X., & Osswald, H. L. (2015). Enantioselective Synthesis of Dioxatriquinane Structural Motifs for HIV-1 Protease Inhibitors Using a Cascade Radical Cyclization. Tetrahedron letters, 56(23), 3314-3317. https://doi.org/10.1016/j.tetlet.2015.01.019
Ghosh, Arun K, et al. "Enantioselective Synthesis of Dioxatriquinane Structural Motifs for HIV-1 Protease Inhibitors Using a Cascade Radical Cyclization." Tetrahedron letters vol. 56,23 (2015): 3314-3317. doi: https://doi.org/10.1016/j.tetlet.2015.01.019
Ghosh AK, Xu CX, Osswald HL. Enantioselective Synthesis of Dioxatriquinane Structural Motifs for HIV-1 Protease Inhibitors Using a Cascade Radical Cyclization. Tetrahedron Lett. 2015 Jun 03;56(23):3314-3317. doi: 10.1016/j.tetlet.2015.01.019. PMID: 26185337; PMCID: PMC4500529.
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Tetrahedron Lett. 2015 Jun 03;56(23):3314-3317. doi: 10.1016/j.tetlet.2015.01.019.

Enantioselective Synthesis of Dioxatriquinane Structural Motifs for HIV-1 Protease Inhibitors Using a Cascade Radical Cyclization.

Tetrahedron letters

Arun K Ghosh, Chun-Xiao Xu, Heather L Osswald

Affiliations

  1. Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.

PMID: 26185337 PMCID: PMC4500529 DOI: 10.1016/j.tetlet.2015.01.019

Abstract

Synthesis of novel HIV-1 protease inhibitors incorporating dioxatriquinane-derived P2-ligands is described. The tricyclic ligand alcohol contains five contiguous chiral centers. The ligand alcohols were prepared in optically active form by an enzymatic asymmetrization of mesodiacetate, cascade radical cyclization, and Lewis acid catalyzed reduction as the key steps. Inhibitors with dioxatriquinane-derived P2-ligands exhibited low nanomolar HIV-1 protease activity.

Keywords: Cascade; Dioxatriquinane; HIV-1 protease; Inhibitor; Radical

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