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Modular, stereocontrolled Cß-H/Cα-C activation of alkyl carboxylic acids.
Shang, Ming; Feu, Karla S; Vantourout, Julien C; Barton, Lisa M; Osswald, Heather L; Kato, Nobutaka; Gagaring, Kerstin; McNamara, Case W; Chen, Gang; Hu, Liang; Ni, Shengyang; Fernández-Canelas, Paula; Chen, Miao; Merchant, Rohan R; Qin, Tian; Schreiber, Stuart L; Melillo, Bruno; Yu, Jin-Quan; Baran, Phil S.
Afiliação
  • Shang M; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Feu KS; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Vantourout JC; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Barton LM; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Osswald HL; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Kato N; Chemical Biology and Therapeutics Science Program, Broad Institute, Cambridge, MA 02142.
  • Gagaring K; Biology Department, Calibr at The Scripps Research Institute, La Jolla, CA 92037.
  • McNamara CW; Biology Department, Calibr at The Scripps Research Institute, La Jolla, CA 92037.
  • Chen G; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Hu L; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Ni S; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Fernández-Canelas P; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Chen M; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Merchant RR; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Qin T; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037.
  • Schreiber SL; Chemical Biology and Therapeutics Science Program, Broad Institute, Cambridge, MA 02142.
  • Melillo B; Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138.
  • Yu JQ; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037; bmelillo@scripps.edu yu200@scripps.edu pbaran@scripps.edu.
  • Baran PS; Chemical Biology and Therapeutics Science Program, Broad Institute, Cambridge, MA 02142.
Proc Natl Acad Sci U S A ; 116(18): 8721-8727, 2019 04 30.
Article em En | MEDLINE | ID: mdl-30996125
ABSTRACT
The union of two powerful transformations, directed C-H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus, amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article
Texto completo
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article