title: Asymmetric total synthesis of (+)-K01-0509 B: determination of absolute configuration.
abstract: K01-0509 B is a novel natural product which contains a carbamoylated cyclic guanidine. Our asymmetric total synthesis features a Sharpless asymmetric epoxidation and a stereocontrolled construction of the cyclic guanidine via an asymmetric nitroaldol reaction, followed by intramolecular SN2 cyclization. These reactions allowed the cyclic guanidine and the adjacent hydroxy group to be assembled, facilitating the asymmetric total synthesis and determination of the absolute stereochemistry of K01-0509 B. [reaction: see text].
authors.affiliation: Kitasato Institute for Life Sciences, Graduate School of Infection Control Sciences, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Tsuchiya
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Sunazuka
authors.forename: Tomoyasu
authors.initials: T
authors.lastname: Hirose
authors.forename: Ryuma
authors.initials: R
authors.lastname: Mori
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Tanaka
authors.forename: Masato
authors.initials: M
authors.lastname: Iwatsuki
authors.forename: Satoshi
authors.initials: S
authors.lastname: Omura
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis; D004983:Ethanolamines; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D004852:Epoxy Compounds; D004983:Ethanolamines; D006146:Guanidines; C522752:K01-0509 B; D003035:Cobalt; C025342:RP333