Synthesis of gem-difluoromethylenated bicyclo[ m.n. 0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones

Teerachai PunirunKrisana PeewasanChutima KuhakarnDarunee SoorukramPatoomratana TuchindaVichai ReutrakulPalangpon KongsaereeSamran PrabpaiManat PohmakotrMahidol University2018-06-112018-06-112012-04-06Organic Letters. Vol.14, No.7 (2012), 1820-182315237052152370602-s2.0-84859567131https://repository.li.mahidol.ac.th/handle/20.500.14594/13760Fluoride-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.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistrySynthesis of gem-difluoromethylenated bicyclo[ m.n. 0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactonesArticleSCOPUS10.1021/ol3004194