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Synlett 2005(3): 365-387  
DOI: 10.1055/s-2005-862382
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Amaryllidaceae Constituents - An Update

Uwe Rinnerb, Tomas Hudlicky*a
a Department of Chemistry, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada
Fax: +1(905)9844841; e-Mail: thudlicky@brocku.ca;
b Institut für Organische Chemie, Universität Wien, Währinger Strasse 38, 1090 Wien, Austria
Fax: +43(0)1427752189; e-Mail: uwe.rinner@univie.ac.at;
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Received 15 June 2004
Publikationsdatum:
04. Februar 2005 (online)

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Abstract

Recent progress in the synthesis of major constituents of the Amaryllidaceae family is reviewed. Total syntheses of pancratistatin, narciclasine, and their 7-deoxy- derivatives, 7-deoxypancratistatin and lycoricidine, respectively, are covered in detail. Also included are preparations of truncated derivatives and unnatural mimics of pancratistatin. The literature coverage begins with the publication of the last major review in 1996 and is complete through the fall of 2004.

  • 1 Introduction

  • 2 Total Syntheses

  • 2.1 Pancratistatin

  • 2.1.1 Haseltine (1997)

  • 2.1.2 Magnus (1998)

  • 2.1.3 Rigby (2000)

  • 2.1.4 Pettit (2001)

  • 2.1.5 Kim (2002)

  • 2.2 7-Deoxypancratistatin

  • 2.2.1 Keck (1998)

  • 2.2.2 Plumet (2000)

  • 2.3 Narciclasine

  • 2.3.1 Rigby (1997)

  • 2.3.2 Hudlicky (1999)

  • 2.3.3 Keck (1999)

  • 2.3.4 Yan (2002)

  • 2.4 Lycoricidine

  • 2.4.1 Keck (1999)

  • 2.4.2 Yan (2002)

  • 3 Unnatural and Truncated Derivatives

  • 3.1 ent-Lycoricidine (Keck, 1996)

  • 3.2 ent-7-Deoxypancratistatin (Hudlicky, 1999)

  • 3.3 Positional Isomer of 7-Deoxypancratistatin (Hudlicky, 2000)

  • 3.4 epi-7-Deoxypancratistatin (Hudlicky, 2001)

  • 3.5 Deoxygenated Derivative of 7-Deoxypancratistatin
    (McNulty, 2001)

  • 3.6 Truncated Derivative of 7-Deoxypancratistatin (Hudlicky, 2002)

  • 3.7 Deoxygenated Derivative of 7-Deoxypancratistatin (Hudlicky, 2004)

  • 3.8 Carbohydrate Analog of 7-Deoxypancratistatin (Fessner, 2004)

  • 3.9 β-Carboline-1-one Analog of Pancratistatin (Hudlicky, 2004)

  • 4 Conclusion

Key words

total synthesis - Amaryllidaceae constituents (alkaloids) - unnatural and truncated derivatives

1

The pancratistatin, narciclasine, and lycoricidine group of natural products has collectively been referred to as ‘Amaryllidaceae alkaloids’ by most, if not all, synthetic chemists (Martin, Hudlicky, Keck, Polt, and others). Such nomenclature is not accurate, as these compounds do not contain basic nitrogen atoms. Another term used in the literature is ‘isocarbostyril’ (Pettit), a term which is not generally known in the synthetic community. To avoid further inaccuracies we will avoid both names in future publications and simply refer to these compounds as ‘constituents’.