Synthesis of (±)-acetylnorloline via stereoselective tethered aminohydroxylation

…, EJ Eklund, RD Pike, AA Mainkar, JR Scheerer

Index: Hovey, M. Todd; Eklund, Emily J.; Pike, Robert D.; Mainkar, Anshul A.; Scheerer, Jonathan R. Organic Letters, 2011 , vol. 13, # 5 p. 1246 - 1249

Full Text: HTML

Citation Number: 16

Abstract

Loline alkaloids exhibit a strained ether-bridged pyrrolizidine skeleton and possess insecticidal and insect antifeedant properties. The synthesis of acetylnorloline, a prototypical member of the alkaloid family, is described. Central to the route is a stereoselective tethered aminohydroxylation (TA) of a homoallylic carbamate. Allylic (A1, 3) strain is exploited to enforce diastereofacial selectivity during the aminohydroxylation.

Related Articles:

Total synthesis of (-)-slaframine from (2R, 3S)-3-hydroxyproline

[Knight, David W.; Sibley, A. William Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 15 p. 2179 - 2187]

New strategies towards proline derivatives as conformationally constrained arginine analogues

[Pellegrini, Nadia; Schmitt, Martine; Guery, Sebastien; Bourguignon, Jean-Jacques Tetrahedron Letters, 2002 , vol. 43, # 17 p. 3243 - 3246]

D-Proline-based peptidomimetic inhibitors of anthrax lethal factor

[Calugi, Chiara; Trabocchi, Andrea; Lalli, Claudia; Guarna, Antonio European Journal of Medicinal Chemistry, 2012 , vol. 56, p. 96 - 107]

More Articles...