title: Total synthesis of methymycin.
abstract: Methynolide and 10-epi-methynolide were synthesized from the necessary segments, which were prepared by the addition of Grignard reagents to the corresponding alpha-alkoxyketones utilizing 1,2-stereochemical selection based on Cram chelation control. Ring-closing metathesis, as the key reaction, was carried out to combine the segments for the synthesis of methynolide and 10-epi-methynolide. The total synthesis of methymycin was also achieved by the glycosylation of methynolide with the trichloroimidate derivative of D-desosamine.
authors.affiliation: Department of Chemistry, Chungbuk National University, Cheongju 361-763, Republic of Korea.
authors.forename: Hong-Se
authors.initials: HS
authors.lastname: Oh
authors.forename: Richeng
authors.initials: R
authors.lastname: Xuan
authors.forename: Han-Young
authors.initials: HY
authors.lastname: Kang
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D018942:Macrolides; C522940:methynolide; C008517:methymycin