Synthesis of (±)-Acetylnorloline via Stereoselective Tethered Aminohydroxylation

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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Beschreibung
Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200155p