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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
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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]
Total Authors: 19
Affiliation:
[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
Total Affiliations: 4
Document type: Journal article
Source: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA; v. 116, n. 18, p. 8721-8727, APR 30 2019.
Web of Science Citations: 3
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. (AU)

FAPESP's process: 17/08128-7 - Total Synthesis of Eremantholide A and C
Grantee:Karla Santos Feu
Support Opportunities: Scholarships abroad - Research Internship - Post-doctor