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Stereoselective Synthesis of the IDO Inhibitor Navoximod.
St-Jean, Frédéric; Angelaud, Rémy; Bachmann, Stephan; Carrera, Diane E; Remarchuk, Travis; Piechowicz, Katarzyna A; Niedermann, Katrin; Iding, Hans; Meier, Roland; Hou, Haiyun; Sirois, Lauren E; Xu, Jie; Olbrich, Martin; Rege, Pankaj; Guillemot-Plass, Maud; Gosselin, Francis.
Afiliação
  • St-Jean F; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Angelaud R; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Bachmann S; Synthetic Molecules Technical Development, F. Hoffmann-La Roche Ltd., Grenzacherstraße 124, 4070 Basel, Switzerland.
  • Carrera DE; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Remarchuk T; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Piechowicz KA; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Niedermann K; Synthetic Molecules Technical Development, F. Hoffmann-La Roche Ltd., Grenzacherstraße 124, 4070 Basel, Switzerland.
  • Iding H; Synthetic Molecules Technical Development, F. Hoffmann-La Roche Ltd., Grenzacherstraße 124, 4070 Basel, Switzerland.
  • Meier R; Synthetic Molecules Technical Development, F. Hoffmann-La Roche Ltd., Grenzacherstraße 124, 4070 Basel, Switzerland.
  • Hou H; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Sirois LE; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Xu J; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
  • Olbrich M; Synthetic Molecules Technical Development, F. Hoffmann-La Roche Ltd., Grenzacherstraße 124, 4070 Basel, Switzerland.
  • Rege P; Synthetic Molecules Technical Development, F. Hoffmann-La Roche Ltd., Grenzacherstraße 124, 4070 Basel, Switzerland.
  • Guillemot-Plass M; Synthetic Molecules Technical Development, F. Hoffmann-La Roche Ltd., Grenzacherstraße 124, 4070 Basel, Switzerland.
  • Gosselin F; Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
J Org Chem ; 87(7): 4955-4960, 2022 04 01.
Article em En | MEDLINE | ID: mdl-35317556
ABSTRACT
A highly efficient asymmetric synthesis of the IDO inhibitor navoximod, featuring the stereoselective installation of two relative and two absolute stereocenters from an advanced racemic intermediate, is described. The stereocenters were set via a crystallization-induced dynamic resolution along with two selective ketone reductions one via a biocatalytic ketoreductase transformation and one via substrate-controlled hydride delivery from LiAlH(Ot-Bu)3. Following this strategy, navoximod was synthesized in 10 steps from 2-fluorobenzaldehyde and isolated in 23% overall yield with 99.7% ee and high purity.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Inibidores Enzimáticos / Indóis Idioma: En Ano de publicação: 2022 Tipo de documento: Article
Texto completo
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PubMed Links
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Inibidores Enzimáticos / Indóis Idioma: En Ano de publicação: 2022 Tipo de documento: Article