Synthesis and antileishmanial activity of the core structure of cristaxenicin A
Hitoshi Fumiyama1, Tomoko Sadayuki1, Yasutaka Osada2
1Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
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.
