title: Synthesis of the pluramycins 2: total synthesis and structure assignment of saptomycin B.
abstract: A concise, highly convergent total synthesis of saptomycin B, a member of the pluramycin class of antitumor antibiotics, is reported. The target compound was assembled from four building blocks (a tricyclic platform, two sugars, and an alkynal) in 15% yield through 10 synthetic operations. The key steps included the regioselective installation of two amino sugars (L-vancosamine and D-angolosamine) on the tricycle and the efficient construction of the tetracyclic skeleton by an aldol reaction followed by formation of the pyranone. The unknown configuration at C14 was assigned as R.
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan) http://www.chemistry.titech.ac.jp/∼org_synth/
authors.forename: Kei
authors.initials: K
authors.lastname: Kitamura
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Maezawa
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Ando
authors.forename: Takenori
authors.initials: T
authors.lastname: Kusumi
authors.forename: Takashi
authors.initials: T
authors.lastname: Matsumoto
authors.forename: Keisuke
authors.initials: K
authors.lastname: Suzuki
mesh_terms: D000606:Amino Sugars / Q000737:chemistry; D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006595:Hexosamines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000606:Amino Sugars; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D006595:Hexosamines; C000591597:saptomycin B; C003169:pluramycin; C001946:vancosamine
keywords: C-glycosylation; amino sugars; antibiotics; pluramycins; total synthesis