Synthesis of (±)-Acetylnorloline via Stereoselective Tethered Aminohydroxylation

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...

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Veröffentlicht in:	Organic letters 2011-03, Vol.13 (5), p.1246-1249
Hauptverfasser:	Hovey, M. Todd, Eklund, Emily J, Pike, Robert D, Mainkar, Anshul A, Scheerer, Jonathan R
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemistry Amines - chemistry Epichloe - chemistry Hydroxylation Lolium - microbiology Molecular Structure Neotyphodium - chemistry Pyrrolizidine Alkaloids - chemical synthesis Pyrrolizidine Alkaloids - chemistry Stereoisomerism
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creator	Hovey, M. Todd Eklund, Emily J Pike, Robert D Mainkar, Anshul A Scheerer, Jonathan R
description	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.
doi_str_mv	10.1021/ol200155p
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subjects	Alkaloids - chemistry Amines - chemistry Epichloe - chemistry Hydroxylation Lolium - microbiology Molecular Structure Neotyphodium - chemistry Pyrrolizidine Alkaloids - chemical synthesis Pyrrolizidine Alkaloids - chemistry Stereoisomerism
title	Synthesis of (±)-Acetylnorloline via Stereoselective Tethered Aminohydroxylation
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