A review showing the efforts toward the isolation, total synthesis and biological activity of phenanthroindolizidine and phenanthroquinolizidine alkaloids from 1981 to 2000 is presented.
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1 Introduction
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2 Isolation of the Alkaloids
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3 Total Synthesis
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3.1 Directed Metallation of Tertiary Phenanthrene Amides
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3.2 Intramolecular Double Michael Reaction
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3.3 Biomimetic Synthesis
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3.4 Highly Enantioselective Amidoalkylations with N-Acylhydrazonium Salts
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3.5 Intramolecular Imino (Immonium) Diels-Alder Reaction
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3.6 Friedel-Crafts Acylation with N-(Trifluoroacetyl)-α-amino Acid Chloride
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3.7 Synthesis of (S)-(+)-Tylophorine or (S)-(+)-Cryptopleurine with (S)-(+)-Glutamic Acid or (S)-(+)-α-Aminoadipic Acid
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3.8 Intramolecular Cycloadditon of Azide with ω-Chloroalkene
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3.9 Thermal Ring Expansion of 4-(1-Pyrrolo)cyclobutenones
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3.10 Through Sterically Congested Pyridines
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3.11 Synthesis of (-)-Septicine and (-)-Tylophorine via Enantiopure N-Acyldihydropyridones
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3.12 Isomünchnone-based Method as Key Step
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3.13 Phosphorylated Cyclic Carbamate as Staring Material
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4 Biological Activity
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5 Conclusions
phenanthroindolizidine alkaloids - total synthesis - natural products - Diels-Alder reactions - intromolecular Michael additions - tylophorine - cryptopleurine
