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

• Main Authors: Teerachai Punirun, Krisana Peewasan, Chutima Kuhakarn, Darunee Soorukram, Patoomratana Tuchinda, Vichai Reutrakul, Palangpon Kongsaeree, Samran Prabpai, Manat Pohmakotr
• Other Authors: Mahidol University
• Format: Article
• Published: 2018
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemistry
• Online Access: https://repository.li.mahidol.ac.th/handle/123456789/13760

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 fol...