title: Evolution of the total syntheses of batzellasides, the first marine piperidine iminosugar.
abstract: Batzellasides A-C are C-alkylated piperidine iminosugars isolated from a sponge, Batzella sp. The first total synthesis of (+)-batzellaside B was achieved by employing a chiral pool approach starting from L-arabinose for the construction of a piperidine ring system. Subsequently, a practical second-generation synthesis was developed by utilizing a Sharpless asymmetric dihydroxylation for the preparation of the common piperidine intermediate elaborated in the first-generation synthesis. The overall yield of batzellaside B was improved to 3.3% by introducing the exocyclic C8 stereocenter via facial selective hydride addition to a linear ketone. These syntheses allowed for the determination of the absolute stereochemistry of this natural product as well as for providing precious samples, which would pave the way for further biological studies.
authors: Department of Applied Chemistry, Graduate School of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu, Shizuoka 432-8561, Japan.
authors: Tetsuya
authors: T
authors: Sengoku
authors: Jolanta
authors: J
authors: Wierzejska
authors: Masaki
authors: M
authors: Takahashi
authors: Hidemi
authors: H
authors: Yoda
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000606:Amino Sugars; C498137:batzellaside B