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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Modular, stereocontrolled C-beta-H/C-alpha-C activation of alkyl carboxylic acids

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Autor(es):
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Shang, Ming [1] ; Feu, Karla S. [1] ; Vantourout, Julien C. [1] ; Barton, Lisa M. [1] ; Osswald, Heather L. [1] ; Kato, Nobutaka [2] ; Gagaring, Kerstin [3] ; McNamara, Case W. [3] ; Chen, Gang [1] ; Hu, Liang [1] ; Ni, Shengyang [1] ; Fernandez-Canelas, Paula [1] ; Chen, Miao [1] ; Merchant, Rohan R. [1] ; Qin, Tian [1] ; Schreiber, Stuart L. [4, 2] ; Melillo, Bruno [1, 2] ; Yu, Jin-Quan [1] ; Baran, Phil S. [1]
Número total de Autores: 19
Afiliação do(s) autor(es):
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 - USA
[2] Broad Inst, Chem Biol & Therapeut Sci Program, Cambridge, MA 02142 - USA
[3] Scripps Res Inst, Biol Dept, Calibr, La Jolla, CA 92037 - USA
[4] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 - USA
Número total de Afiliações: 4
Tipo de documento: Artigo Científico
Fonte: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA; v. 116, n. 18, p. 8721-8727, APR 30 2019.
Citações Web of Science: 3
Resumo

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. (AU)

Processo FAPESP: 17/08128-7 - Síntese Total das Eremantolidas A e C
Beneficiário:Karla Santos Feu
Linha de fomento: Bolsas no Exterior - Estágio de Pesquisa - Pós-Doutorado