title: Synthesis of Demissidine and Solanidine.
abstract: Demissidine and solanidine, two steroidal alkaloids, are synthesized in eight steps from tigogenin acetate and diosgenin acetate, respectively, which involve the replacement of three C-O bonds with C-N bonds. Key transformations include a cascade ring-switching process of furostan-26-acid, an epimerization of C25, an intramolecular Schmidt reaction, and an imine reduction/intramolecular aminolysis process.
authors.affiliation: Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University , 100 Guilin Road, Shanghai 200234, China.
authors.forename: Zhi-Dan
authors.initials: ZD
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Shi
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Jing-Jing
authors.initials: JJ
authors.lastname: Wu
authors.affiliation: Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University , 100 Guilin Road, Shanghai 200234, China.
authors.forename: Jing-Rong
authors.initials: JR
authors.lastname: Lin
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Wei-Sheng
authors.initials: WS
authors.lastname: Tian