Synthesis of (+)-anatoxin-a using enyne metathesis |
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Authors: | Miwako Mori Tomohiro Tomita Yoichi Kita Tsuyoshi Kitamura |
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Institution: | Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan |
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Abstract: | Synthesis of N-tosylanatoxin-a was achieved by metathesis of enyne in cis-substituents on a pyrrolidine derivative. Metathesis reactions of enyne having terminal alkyne using various ruthenium-carbene complexes did not give a good results. However, when the terminal alkyne was protected with a TMS group, the reaction proceeded smoothly using a second-generation ruthenium-carbene complex to give the desired cyclized compound in high yield. Oxymercuration followed by Dess-Martin oxidation afforded N-tosylanatoxin-a. |
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Keywords: | Anatoxin-a N-tosylanatoxin-a Enyne metathesis Pyrrolidine derivative Second-generation ruthenium-carbene complex |
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