Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an Enabling Oxidation Strategy

Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an Enabling Oxidation Strategy
Neil A. Strotman, Scott A. Savage, Zhongmin Xu, Jeffrey Nye, Matthew Haley, Sloan Ayers, Susanne Kiau, Adrian Ortiz, Maxime Soumeillant, Yichen Tan, Qi Gao, Tamas Benkovics
A concise and scalable second generation synthesis of HIV maturation inhibitor BMS-955176 is described. The synthesis is framed by an oxidation strategy highlighted by a CuI mediated aerobic oxidation of betulin, a highly selective PIFA mediated dehydrogenation of an oxime, and a subsequent Lossen rearrangement which occurs through a unique reaction mechanism for the installation of the C17 amino functionality. The synthetic route proceeds in 7 steps with 47% overall yield and begins from the abundant and inexpensive natural product betulin.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00438

DOI: 10.1021/acs.joc.7b00438

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