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Title: Synthesis of gem-difluoromethylenated bicyclo[ m.n. 0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones
Authors: Teerachai Punirun
Krisana Peewasan
Chutima Kuhakarn
Darunee Soorukram
Patoomratana Tuchinda
Vichai Reutrakul
Palangpon Kongsaeree
Samran Prabpai
Manat Pohmakotr
Mahidol University
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry
Issue Date: 6-Apr-2012
Citation: Organic Letters. Vol.14, No.7 (2012), 1820-1823
Abstract: Fluoride-catalyzed stereoselective nucleophilic addition of PhSCF 2 SiMe 3 (1) to α-carboethoxycycloalkanones 2 followed by intramolecular radical cyclization of the resulting cis-3 adduct afforded the corresponding gem-difluoromethylenated bicyclic compounds 4, which underwent ring-expansion followed by the Baeyer-Villiger-type oxidation of the resulting macrocyclic ketone intermediates to give gem-difluoromethylenated macrocyclic lactones 5. © 2012 American Chemical Society.
ISSN: 15237052
Appears in Collections:Scopus 2011-2015

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