Transition-metal catalyzed asymmetric transformations have proven to be a highly efficient and enabling methodology to induce desired chirality. In our laboratory, a library of biphenol-based phosphoramidite ligands has been developed, which is very effective in the Pd-catalyzed asymmetric allylic alkylation for the total synthesis of (+)-?-Lycorane with >99% ee. (-)-Huperzine A, isolated from the plant firmoss, Huperzia serrata, is an acetylcholinesterase (AChE) inhibitor and shows promise in the treatment of Alzheimer's disease and enhance memor. We present here a highly efficient Pd-catalyzed asymmetric tandem allylic alkylation process for the synthesis of an advanced key intermediate to (-)-Huperzine A with excellent enantioseletivity using novel phosphoramidite ligands.

Asymmetric synthesis of an advanced key intermediate to (-)-Huperzine A via Pd-catalyzed intermolecular tandem allylic alkylation using chiral biphenol-based phosphoramidites

244th National Meeting (2012)

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