title: A new approach toward the total synthesis of (+)-batzellaside B.
abstract: A new synthetic approach to (+)-batzellaside B from naturally abundant L-pyroglutamic acid is presented in this article. The key synthetic step involves Sharpless asymmetric dihydroxylation of an olefinic substrate functionalized with an acetoxy group to introduce two chiral centres diastereoselectively into the structure. Heterocyclic hemiaminal 4, which could be converted from the resulting product, was found to provide stereospecific access to enantiomerically enriched allylated intermediate, offering better prospects for the total synthesis of this natural product.
authors.affiliation: Department of Materials Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu, Shizuoka 432-8561, Japan.
authors.forename: Jolanta
authors.initials: J
authors.lastname: Wierzejska
authors.forename: Shin-Ichi
authors.initials: S
authors.lastname: Motogoe
authors.forename: Yuto
authors.initials: Y
authors.lastname: Makino
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