title: Total synthesis of paracentrone, C31-allenic apo-carotenoid.
abstract: The stereocontrolled total synthesis of a C31-allenic apo-carotenoid, paracentrone, was achieved by the convergent C20 + C11 = C31 strategy. The key elements of our synthesis were the Pd-catalyzed cross-coupling to stereoselectively construct the conjugated polyene backbone skeleton and the designed geometrical isomerization at the central double bond of the conjugated polyene chain. In addition, the terminal oxygenated cyclohexane ring having the allenic moiety was prepared by the highly diastereoselective Sharpless epoxidation under our own reaction conditions.
authors.affiliation: School of Science and Technology, Kwansei Gakuin University, Sanda, Hyogo, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Murakami
authors.forename: Masayuki
authors.initials: M
authors.lastname: Nakano
authors.forename: Takuya
authors.initials: T
authors.lastname: Shimofusa
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Furuichi
authors.forename: Shigeo
authors.initials: S
authors.lastname: Katsumura
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002338:Carotenoids / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000447:Aldehydes; D007454:Iodides; C511164:paracentrone; D002338:Carotenoids