Magellanine Explained

(−)-Magellanine is a member of the Lycopodium alkaloid class of natural products. It was isolated from the club moss Lycopodium magellanicum in 1976.^[1] It has been synthesized five times, with the first synthesis having been completed by the Larry E. Overman group at the University of California, Irvine in 1993.^[2] It has also been synthesized by the Leo Paquette group in 1993 at Ohio State University,^[3] the Chun-Chen Liao group in 2002 at National Tsing Hua University,^[4] the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the Josai International University and Tokyo University of Science,^[5] and the Chisato Mukai group in 2007 at the Kanazawa University.^[6] One partial synthesis was completed by the A. I. Meyers group in 1995 at Colorado State University.^[7]

Biosynthetically, it is thought to have been derived from lysine. This was determined by conducting feeding studies of radiolabeled precursors.^[8]

References

1. 1976 . Isolation and Structure . Canadian Journal of Chemistry . 54 . 18. 2893–2899 . 10.1139/v76-409 . Castillo . Mariano . Loyola . Luis A. . Morales . Glauco . Singh . Ishwar . Calvo . Crispin . Rolland . Herbert L. . MacLean . David B.. free .
2. 10.1021/ja00060a064 . 115 . 7 . First total synthesis of Lycopodium alkaloids of the magellanane group. Enantioselective total syntheses of (-)-magellanine and (+)-magellaninone . 1993 . Journal of the American Chemical Society . 2992–2993 . Hirst . Gavin C..
3. 10.1021/ja00090a017 . 116 . 11 . Total Synthesis of the Lycopodium Alkaloids Magellanine and Magellaninone by Three-fold Annulation of 2-Cyclopentenone . 1994 . Journal of the American Chemical Society . 4689–4696 . Williams . John P..
4. 10.1002/1521-3773(20021104)41:21<4090::AID-ANIE4090>3.0.CO;2-# . 41 . 21 . Concise and Efficient Total Synthesis of Lycopodium Alkaloid Magellanine . 2002 . Angewandte Chemie International Edition . 4090–4093 . Yen . Chi-Feng.
5. 10.1016/j.tet.2005.02.044 . 61 . 16 . A formal total synthesis of Lycopodium alkaloid, (±)-magellanine, by using the intramolecular Pauson Khand reaction . 2005 . Tetrahedron . 4053–4065 . Ishizaki . Miyuki . Niimi . Yuka . Hoshino . Osamu . Hara . Hiroshi . Takahashi . Tamiko.
6. 10.1002/chin.200818182 . 39 . 18 . ChemInform Abstract: Stereoselective Total Synthesis of Three Lycopodium Alkaloids, (-)-Magellanine (I), (+)-Magellaninone (II), and (+)-Paniculatine (III), Based on Two Pauson—Khand Reactions. . 2008 . ChemInform . Kozaka . Takashi.
7. Meyers . A. I. . Partial Synthesis . J. Chem. Soc. Chem. Commun.. 1995 . 2511–2512 .
8. 2004 . Biosynthesis of the Lycopodium Alkaloids . Nat. Prod. Rep. . 21 . 752–772 . 10.1039/b409720n . Ma . Xiaoqiang . Gang . David R..