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
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
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