title: Total Synthesis of Thailandepsin B, a Potent HDAC Inhibitor Isolated from a Microorganism.
abstract: Thailandepsin B, a bicyclic depsipeptide histone deacetylase inhibitor, was efficiently synthesized in 51% overall yield in eight steps, starting from commercially available D-norleucine methyl ester and known (S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoic acid. The method features a convergent approach in which the corresponding seco-acid, a key precursor in macrolactonization, is directly assembled through the condensation of a D-allo-isoleucine-D-cysteine-containing segment with a D-norleucine-containing segment.
authors.affiliation: Laboratory of Synthetic and Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University.
authors.forename: Koichi
authors.initials: K
authors.lastname: Narita
authors.forename: Tadashi
authors.initials: T
authors.lastname: Katoh
mesh_terms: D019117:Burkholderia / Q000201:enzymology*; D047630:Depsipeptides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D056572:Histone Deacetylase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006655:Histone Deacetylases / Q000378:metabolism*; D008968:Molecular Conformation
chemical_list: D047630:Depsipeptides; D056572:Histone Deacetylase Inhibitors; C000613661:thailandepsin B; D006655:Histone Deacetylases