title: Total Synthesis and Stereochemical Assignment of Callyspongiolide.
abstract: Total synthesis of four callyspongiolide stereoisomers led to unambiguous assignment of relative and absolute stereochemistry of the natural product. Key features of the convergent, fully stereocontrolled route include the use of Krische allylation, Kiyooka Aldol reaction, Kociénski-Julia olefination, Still-Gennari olefination, Yamaguchi macrocyclization, and Sonogashira coupling reaction. Biological evaluation of the synthesized compounds against an array of cancer cells revealed that the stereochemistry of the macrolactone core played an important role.
authors.affiliation: Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Xili, Nanshan District, Shenzhen 518055, China.
authors.forename: Jingjing
authors.initials: J
authors.lastname: Zhou
authors.affiliation: Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Xili, Nanshan District, Shenzhen 518055, China.
authors.forename: Bowen
authors.initials: B
authors.lastname: Gao
authors.affiliation: Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Xili, Nanshan District, Shenzhen 518055, China.
authors.forename: Zhengshuang
authors.initials: Z
authors.lastname: Xu
authors.affiliation: Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Xili, Nanshan District, Shenzhen 518055, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Ye
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D006801:Humans; D020128:Inhibitory Concentration 50; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D018942:Macrolides; C588104:callyspongiolide