Synthetic studies on amaryllidaceae and other terrestrially derived alkaloids
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Abstract
The total syntheses of a wide range of terrestrially derived alkaloids, especially ones isolated from members of the Amaryllidaceae family, are described. Two recurring themes associated with these syntheses are the use of two types of building blocks, namely ring-fused cyclopropanes, especially geminally-dihalogenated ones, and enzymatically derived cis-1,2- dihydrocatechols. These have often served as precursors to 2-or 3-halogenated 2-cyclohexen-1-ols that are themselves engaged in cross-coupling reactions, radical addition-elimination processes and/or Claisen-or Overman-type rearrangements so as to construct the highly functionalized six-membered rings associated with the target alkaloids.
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γ-Lycorane, Alkaloids, Amabiline, Amaryllidaceae, Aspidospermidine, Brunsvigine, Colchicine, Corey-Winter reaction, Cross-coupling, Cyclopropane, epi-Maritinamine, Erythramine, Eschenmoser-Claisen rearrangement, Galanthamine, Grandirubrine, Haemultine, Imerubrine, Ireland-Claisen rearrangement, Lycoricidine, Maritinamine, Mitsunobu reaction, Nangustine, Narciclasine, Overman rearrangement, Pancracine, Pictet-Spengler reaction, Radical cyclisation, Rhazinal, Rhazinilam, Suzuki-Miyaura reaction, Ullmann reaction, Wittig reaction
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Alkaloid Synthesis
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