title: Stereocontrolled total synthesis of a polyfunctional carotenoid, peridinin.
abstract: Peridinin, which was isolated from the planktonic algae dinoflagellates causing red tides, is a highly oxidized carotenoid containing an allene and a characteristic (Z)-gamma-ylidenebutenolide function in the main conjugated polyene chain in addition to functionalized cyclohexane rings at both ends of the molecule. We achieved a stereocontrolled total synthesis of peridinin by featuring the Sharpless asymmetric epoxidation under precise reaction conditions, Wittig reaction with silylfuranmethylide followed by photosensitized oxygenation, stereocontrolled Pd-catalyzed one-pot (Z)-gamma-ylidenebutenolide synthesis, and modified Julia-Kocienski olefination. This synthesis is the first example of controlling the stereochemistry of polyfunctional allenic carotenoids.
authors.affiliation: School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo 669-1337, Japan.
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Furuichi
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Hara
authors.forename: Takashi
authors.initials: T
authors.lastname: Osaki
authors.forename: Masayuki
authors.initials: M
authors.lastname: Nakano
authors.forename: Hajime
authors.initials: H
authors.lastname: Mori
authors.forename: Shigeo
authors.initials: S
authors.lastname: Katsumura
mesh_terms: D002338:Carotenoids / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D019906:Nuclear Magnetic Resonance, Biomolecular; D010165:Palladium / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; C016040:peridinin; D002338:Carotenoids; D010165:Palladium