From Wikipedia, the free encyclopedia
Jump to: navigation, search
IUPAC name
3D model (Jmol)
Molar mass 275.39 g·mol−1
Melting point 165 to 166 °C (329 to 331 °F; 438 to 439 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

(−)-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 The 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]


  1. ^ a b Isolation and Structure Canadian Journal of Chemistry, 1976, 54:(18) 2893-2899.
  2. ^ Larry E. Overman Synthesis. J. Am. Chem. Soc., 1993, 115 (7), pp 2992–2993.
  3. ^ Leo Paquette Synthesis J. Am. Chem. Soc., 1994, 116 (11), pp 4689–4696.
  4. ^ Chun-Chen Liao Synthesis Angew. Chem. Int. Ed. 2002, 41, No. 21, 4090-4093.
  5. ^ Miyuki Ishikazi and Yamiko Takahashi Synthesis Tetrahedron 61 (2005) 4053–4065.
  6. ^ Chisato Mukai Synthesis J. Org. Chem. 2007, 26, 10147-10154.
  7. ^ A. I. Meyers Partial Synthesis J. Chem. Soc., Chem. Commun., 1995, 2511-2512.
  8. ^ Biosynthesis of the Lycopodium Alkaloids Nat. Prod. Rep., 2004, 21, 752-772.