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The formal total synthesis of (+)-anatoxin-a was accomplished using enyne metathesis as a key step. It is very interesting that (+)-anatoxin-a was synthesized from (S)-pyroglutamic acid via an unusual inversion of chirality, which is rationalized in terms of a skeletal rearrangement of 9-azabicyclo[4.2.1]nonene derivative at the stage of oxymercuration of the diene.
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...
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