Stereo-controlled synthesis of analogs of peumusolide A, NES non-antagonistic inhibitor for nuclear export of MEK

Stereo-controlled construction of the core structure of peumusolide A (1), α-alkylidene-β-hydroxy-γ-methylenebutyrolactone, was developed by a combination of regio- and stereo-selective hydroiodination of 2-yn-1-ol and asymmetric reduction of 1-yn-4-en-3-one as the key reactions. By using this protocol, all the four stereoisomers of the analog of 1 were synthesized from the common starting material.

Stereo-controlled construction of the core structure of peumusolide A (1), α-alkylidene-β-hydroxy-γ-methylenebutyrolactone, was developed by a combination of regio- and stereo-selective hydroiodination of 2-yn-1-ol and asymmetric reduction of 1-yn-4-en-3-one as the key reactions.