Synthesis of gem-difluoromethylenated bicyclo[m.n.0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones |
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| Authors: | Punirun Teerachai Peewasan Krisana Kuhakarn Chutima Soorukram Darunee Tuchinda Patoomratana Reutrakul Vichai Kongsaeree Palangpon Prabpai Samran Pohmakotr Manat |
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| Institution: | Center of Excellence for Innovation in Chemistry and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. |
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| 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. |
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