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Synthesis 2001(16): 2365-2378
DOI: 10.1055/s-2001-18703
REVIEW
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 13 August 2001
Publication Date:
05 August 2004 (online)

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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