Magellanine

Magellanine
IUPAC name

(4aS,6S,6aR,6bS,10aS,11aS)-6-Hydroxy-3,9-dimethyl-4,4a,5,6,6a,6b,7,8,9,10,10a,11-dodecahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one
Identifiers
CAS number 61273-75-4 Y
PubChem 442489
ChemSpider 390919 Y
Jmol-3D images Image 1
Properties
Molecular formula C17H25NO2
Molar mass 275.39 g mol−1
Melting point

165-166 °C[1]
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

References

  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.