title: Synthesis of (-)-pericosine B, the antipode of the cytotoxic marine natural product.
abstract: The stereoselective synthesis of (-)-pericosine B, which is the antipode of the cytotoxic metabolite of the fungus Periconia byssoides OUPS-N133 separated from the sea hare, was accomplished in 9 steps in 12% total yield from (-)-quinic acid, together with the synthesis of its epimer. Every crucial step of this total synthesis, including ring opening of a beta-epoxide and NaBH4 reduction of an unstable beta,gamma-unsaturated enone, proceeded with excellent stereoselectivity.
authors.affiliation: Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Usami
authors.forename: Kentaro
authors.initials: K
authors.lastname: Suzuki
authors.forename: Koji
authors.initials: K
authors.lastname: Mizuki
authors.forename: Hayato
authors.initials: H
authors.lastname: Ichikawa
authors.forename: Masao
authors.initials: M
authors.lastname: Arimoto
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000633:toxicity; D045744:Cell Line, Tumor; D006801:Humans; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000633:toxicity; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; C496389:pericosine B; D012765:Shikimic Acid