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Building C(sp3)-rich complexity by combining cycloaddition and C-C cross-coupling reactions.
Chen, Tie-Gen; Barton, Lisa M; Lin, Yutong; Tsien, Jet; Kossler, David; Bastida, Iñaki; Asai, Shota; Bi, Cheng; Chen, Jason S; Shan, Mingde; Fang, Hui; Fang, Francis G; Choi, Hyeong-Wook; Hawkins, Lynn; Qin, Tian; Baran, Phil S.
Afiliação
  • Chen TG; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Barton LM; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Lin Y; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Tsien J; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Kossler D; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Bastida I; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Asai S; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Bi C; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Chen JS; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Shan M; Integrated Chemistry Engine, Eisai AiM Institute, Andover, MA, USA.
  • Fang H; Integrated Chemistry Engine, Eisai AiM Institute, Andover, MA, USA.
  • Fang FG; Integrated Chemistry Engine, Eisai AiM Institute, Andover, MA, USA.
  • Choi HW; Integrated Chemistry Engine, Eisai AiM Institute, Andover, MA, USA.
  • Hawkins L; Integrated Chemistry Engine, Eisai AiM Institute, Andover, MA, USA.
  • Qin T; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA.
  • Baran PS; Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA, USA. pbaran@scripps.edu.
Nature ; 560(7718): 350-354, 2018 08.
Article em En | MEDLINE | ID: mdl-30061620
Prized for their ability to rapidly generate chemical complexity by building new ring systems and stereocentres1, cycloaddition reactions have featured in numerous total syntheses2 and are a key component in the education of chemistry students3. Similarly, carbon-carbon (C-C) cross-coupling methods are integral to synthesis because of their programmability, modularity and reliability4. Within the area of drug discovery, an overreliance on cross-coupling has led to a disproportionate representation of flat architectures that are rich in carbon atoms with orbitals hybridized in an sp2 manner5. Despite the ability of cycloadditions to introduce multiple carbon sp3 centres in a single step, they are less used6. This is probably because of their lack of modularity, stemming from the idiosyncratic steric and electronic rules for each specific type of cycloaddition. Here we demonstrate a strategy for combining the optimal features of these two chemical transformations into one simple sequence, to enable the modular, enantioselective, scalable and programmable preparation of useful building blocks, natural products and lead scaffolds for drug discovery.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Carbono / Técnicas de Química Sintética / Reação de Cicloadição Idioma: En Revista: Nature Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Carbono / Técnicas de Química Sintética / Reação de Cicloadição Idioma: En Revista: Nature Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Estados Unidos