Cycloclavine

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Cycloclavine
Cycloclavine.svg
Identifiers
3D model (JSmol)
ChemSpider
Properties
C16H18N2
Molar mass 238.33 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cycloclavine is an ergot alkaloid. It was first isolated in 1969 from seeds of Ipomoea hildebrandtii vatke.[1] The first total synthesis of (±)-cycloclavine was published in 2008 by Szántay.[2] Further reports came from Wipf and Petronijevic,[3] Cao[4] and Brewer.[5] In 2016, Wipf and McCabe completed an 8-step asymmetric synthesis of (-)-cycloclavine.[6]

References[edit]

  1. ^ Stauffacher, D.; Niklaus, P.; Tscherter, H.; Weber, H. P.; Hofmann, A. Tetrahedron 1969, 25, 5879-5887.
  2. ^ Incze, M.; Dörnyei, G.; Moldvai, I.; Temesvári-Major, E.; Egyed, O.; Szántay, C. (2008). "New routes to clavine-type ergot alkaloids. Part 2: Synthesis of the last, so far not yet synthesized member of the clavine alkaloid family, (±)-cycloclavine". Tetrahedron. 64: 2924–2929. doi:10.1016/j.tet.2008.01.101. 
  3. ^ Petronijevic, F. R.; Wipf, P (2011). "Total Synthesis of (±)-Cycloclavine and (±)-5-epi-Cycloclavine". J. Am. Chem. Soc. 133: 7704–7707. doi:10.1021/ja2026882. 
  4. ^ Wang, W.; Lu, J.-T.; Zhang, H.-L.; Shi, Z.-F.; Wen, J.; Cao, X.-P (2013). "Formal Synthesis of (±)-Cycloclavine". J. Org. Chem. 79: 122–127. doi:10.1021/jo4023588. 
  5. ^ Jabre, N. D.; Watanabe, T.; Brewer, M. (2014). "Formal and total synthesis of (±)-cycloclavine". Tetrahedron Lett. 55: 197–199. doi:10.1016/j.tetlet.2013.10.152. 
  6. ^ McCabe, Stephanie R. "Eight-Step Enantioselective Total Synthesis of (−)-Cycloclavine". Angewandte Chemie. 129: 330–333. doi:10.1002/ange.201608820.