title: Synthesis and antileishmanial activity of the core structure of cristaxenicin A.
abstract: The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a β-alkoxy-α,β-unsaturated ketone. The nine membered ring possessing α,β-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC50 value of 2.4μM.
authors.affiliation: Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Fumiyama
authors.affiliation: Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
authors.forename: Tomoko
authors.initials: T
authors.lastname: Sadayuki
authors.affiliation: Department of Animal Resource Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo, Tokyo 1138657, Japan.
authors.forename: Yasutaka
authors.initials: Y
authors.lastname: Osada
authors.affiliation: Department of Animal Resource Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo, Tokyo 1138657, Japan.
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Goto
authors.affiliation: Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan; Research Institute for Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Nakao
authors.affiliation: Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan; Research Institute for Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
authors.forename: Seijiro
authors.initials: S
authors.lastname: Hosokawa
mesh_terms: D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D007891:Leishmania / Q000187:drug effects*; D015394:Molecular Structure
chemical_list: D000981:Antiprotozoal Agents; D004224:Diterpenes; C581652:cristaxenicin A
keywords: Antileishmanial; Cristaxenicin A; Nine-membered ring; Synthesis; [4+2] cycloaddition