title: Synthesis and absolute configuration of demethyl (C-11) cezomycin.
abstract: The synthesis of (-)-demethyl (C-11) cezomycin was achieved through an efficient route that features the use of a Kulinkovich reaction to couple two multifunctionality-containing fragments and a cascade of ring opening of cyclopropanol/1,5-hydrogen shift/desilylation-oxidation. The hidden yet undeniable problem of irreproducible specific rotation for this family of compounds was solved by sufficient acidification. The absolute configuration for the natural product was thus established as the mirror image of the synthetic sample.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institution of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
authors.forename: Shao-Gang
authors.initials: SG
authors.lastname: Li
authors.forename: Yikang
authors.initials: Y
authors.lastname: Wu
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000001:Calcimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000001:Calcimycin; D006859:Hydrogen; C036715:cezomycin
keywords: antibiotics; ketals; natural products; oxidation; total synthesis