title: Synthesis of marine natural product (-)-pericosine E.
abstract: The first synthesis of (-)-pericosine E (6), a metabolite of the Periconia byssoides OUPS-N133 isolated originally from the sea hare Aplysia kurodai, has been achieved. Efficient and regioselective synthetic procedures for the synthesis of key intermediates, anti- and syn-epoxides 9 and 10, were developed using an anti-epoxidation of diene 12 with TFDO and a bromohydrination of 12 with NBS in CH(3)CN/H(2)O (2:3), respectively. In addition, comparison of the specific optical rotations between synthetic 6 and natural 6 elucidated that the naturally preferred enantiomer of pericosine E had the same absolute configuration as (-)-6 synthesized from chlorohydrin (-)-8 and anti-epoxide (+)-9.
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences , 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Mizuki
authors.forename: Kaoru
authors.initials: K
authors.lastname: Iwahashi
authors.forename: Naoko
authors.initials: N
authors.lastname: Murata
authors.forename: Mayuko
authors.initials: M
authors.lastname: Ikeda
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Nakai
authors.forename: Hiroki
authors.initials: H
authors.lastname: Yoneyama
authors.forename: Shinya
authors.initials: S
authors.lastname: Harusawa
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Usami
mesh_terms: D000818:Animals; D001048:Aplysia / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; C000596831:pericosine E; D012765:Shikimic Acid