title: Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon.
abstract: A formal synthesis of (+)-madindoline A was achieved. The Sunazuka's key intermediate, (4R,5S)-(-)-3-butyl-4-(tert-butyldimethylsiloxy)-5-methoxycarbonyl-2,5-dimethyl-2-cyclopentenone, was synthesized from easily available (2S,3S)-3-acetoxy-2-ethenyl-2-methylcyclopentanone. The starting material was reliably supplied by a chemo-enzymatic procedure in enantiomerically pure form. The synthesis was performed by straightforward transformations involving enone formation and regioselective introduction of the two alkyl side chains.
authors: Department of Pharmaceutical Science, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
authors: Ken-ichi
authors: K
authors: Shimizu
authors: Mina
authors: M
authors: Tomita
authors: Ken-ichi
authors: K
authors: Fuhshuku
authors: Takeshi
authors: T
authors: Sugai
authors: Mitsuru
authors: M
authors: Shoji
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D000093242:Interleukin-6 Inhibitors
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D007211:Indoles; D000093242:Interleukin-6 Inhibitors; C103158:madindoline A