title: First total synthesis of epicoccarine A via O- to C-acyl rearrangement strategy.
abstract: The first total synthesis of antibacterial epicoccarine A isolated from a fungus Epicoccum sp. has been accomplished in 10 steps along with synthetic elaboration of its C5-epimer, highlighting the utility of O- to C-acyl rearrangement of a 4-O-acyltetramic acid derivative. Comparison of spectroscopic properties and specific optical rotations of the synthetic samples with those reported for authentic material has clearly indicated the unspecified absolute stereochemistry of this natural product to be 5S.
authors.affiliation: Department of Materials Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu, Shizuoka 432-8561, Japan.
authors.forename: Yasuaki
authors.initials: Y
authors.lastname: Ujihara
authors.forename: Ken
authors.initials: K
authors.lastname: Nakayama
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Sengoku
authors.forename: Masaki
authors.initials: M
authors.lastname: Takahashi
authors.forename: Hidemi
authors.initials: H
authors.lastname: Yoda
mesh_terms: D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011760:Pyrrolidinones; C522278:epicoccarine A