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Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an Enabling Oxidation Strategy.
Ortiz, Adrian; Soumeillant, Maxime; Savage, Scott A; Strotman, Neil A; Haley, Matthew; Benkovics, Tamas; Nye, Jeffrey; Xu, Zhongmin; Tan, Yichen; Ayers, Sloan; Gao, Qi; Kiau, Susanne.
Afiliação
  • Ortiz A; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Soumeillant M; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Savage SA; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Strotman NA; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Haley M; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Benkovics T; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Nye J; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Xu Z; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Tan Y; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Ayers S; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Gao Q; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
  • Kiau S; Chemical and Synthetic Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
J Org Chem ; 82(9): 4958-4963, 2017 05 05.
Article em En | MEDLINE | ID: mdl-28406018
ABSTRACT
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Triterpenos / Fármacos Anti-HIV Idioma: En Ano de publicação: 2017 Tipo de documento: Article
Texto completo
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XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Triterpenos / Fármacos Anti-HIV Idioma: En Ano de publicação: 2017 Tipo de documento: Article