Synthesis of (±)-acetylnorloline via stereoselective tethered aminohydroxylation

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

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

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被引用次数: 16

摘要

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.