Magellanine
Names
Preferred 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
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1 checkY
    Key: ADRPSBGLUHNVOU-INSRFAMQSA-N checkY
  • InChI=1/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1
    Key: ADRPSBGLUHNVOU-INSRFAMQBF
  • O=C1/C=C(/C)C[C@@H]2[C@@]14[C@H]([C@@H](O)C2)[C@@H]3[C@@H](CN(C)CC3)C4
Properties
C17H25NO2
Molar mass 275.392 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).
checkY verify (what is checkY☒N ?)
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 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. 1 2 Castillo, Mariano; Loyola, Luis A.; Morales, Glauco; Singh, Ishwar; Calvo, Crispin; Rolland, Herbert L.; MacLean, David B. (1976). "Isolation and Structure". Canadian Journal of Chemistry. 54 (18): 2893–2899. doi:10.1139/v76-409.
  2. ↑ Hirst, Gavin C. (1993). "First total synthesis of Lycopodium alkaloids of the magellanane group. Enantioselective total syntheses of (-)-magellanine and (+)-magellaninone". Journal of the American Chemical Society. 115 (7): 2992–2993. doi:10.1021/ja00060a064.
  3. ↑ Williams, John P. (1994). "Total Synthesis of the Lycopodium Alkaloids Magellanine and Magellaninone by Three-fold Annulation of 2-Cyclopentenone". Journal of the American Chemical Society. 116 (11): 4689–4696. doi:10.1021/ja00090a017.
  4. ↑ Yen, Chi-Feng (2002). "Concise and Efficient Total Synthesis of Lycopodium Alkaloid Magellanine". Angewandte Chemie International Edition. 41 (21): 4090–4093. doi:10.1002/1521-3773(20021104)41:21<4090::AID-ANIE4090>3.0.CO;2-#.
  5. ↑ Ishizaki, Miyuki; Niimi, Yuka; Hoshino, Osamu; Hara, Hiroshi; Takahashi, Tamiko (2005). "A formal total synthesis of Lycopodium alkaloid, (±)-magellanine, by using the intramolecular Pauson Khand reaction". Tetrahedron. 61 (16): 4053–4065. doi:10.1016/j.tet.2005.02.044.
  6. ↑ Kozaka, Takashi (2008). "ChemInform Abstract: Stereoselective Total Synthesis of Three Lycopodium Alkaloids, (-)-Magellanine (I), (+)-Magellaninone (II), and (+)-Paniculatine (III), Based on Two Pauson—Khand Reactions". ChemInform. 39 (18). doi:10.1002/chin.200818182.
  7. ↑ Meyers, A. I. "Partial Synthesis". J. Chem. Soc. Chem. Commun. 1995: 2511–2512.
  8. ↑ Ma, Xiaoqiang; Gang, David R. (2004). "Biosynthesis of the Lycopodium Alkaloids". Nat. Prod. Rep. 21: 752–772. doi:10.1039/b409720n.
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