Isolation, Total Synthesis and Biological Activity of Phenanthroindolizidine and Phenanthroquinolizidine Alkaloids

Zaiguo Li; Zhong Jin; Runqiu Huang

doi:10.1055/s-2001-18703

REVIEW

Isolation, Total Synthesis and Biological Activity of Phenanthroindolizidine and Phenanthroquinolizidine Alkaloids

Zaiguo Li, Zhong Jin, Runqiu Huang*
Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. China
e-Mail: rqhuang@163.com;

Abstract

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Abstract

A review showing the efforts toward the isolation, total synthesis and biological activity of phenanthroindolizidine and phenanthroquinolizidine alkaloids from 1981 to 2000 is presented.

1 Introduction
2 Isolation of the Alkaloids
3 Total Synthesis
3.1 Directed Metallation of Tertiary Phenanthrene Amides
3.2 Intramolecular Double Michael Reaction
3.3 Biomimetic Synthesis
3.4 Highly Enantioselective Amidoalkylations with N-Acylhydrazonium Salts
3.5 Intramolecular Imino (Immonium) Diels-Alder Reaction
3.6 Friedel-Crafts Acylation with N-(Trifluoroacetyl)-α-amino Acid Chloride
3.7 Synthesis of (S)-(+)-Tylophorine or (S)-(+)-Cryptopleurine with (S)-(+)-Glutamic Acid or (S)-(+)-α-Aminoadipic Acid
3.8 Intramolecular Cycloadditon of Azide with ω-Chloroalkene
3.9 Thermal Ring Expansion of 4-(1-Pyrrolo)cyclobutenones
3.10 Through Sterically Congested Pyridines
3.11 Synthesis of (-)-Septicine and (-)-Tylophorine via Enantiopure N-Acyldihydropyridones
3.12 Isomünchnone-based Method as Key Step
3.13 Phosphorylated Cyclic Carbamate as Staring Material
4 Biological Activity
5 Conclusions

Key words

phenanthroindolizidine alkaloids - total synthesis - natural products - Diels-Alder reactions - intromolecular Michael additions - tylophorine - cryptopleurine

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