Synthesis of (+)-coniceine via reductive photocyclization of dienamides: an entry to indolizidines

Synthesis of (+)-coniceine via reductive photocyclization of dienamides: an entry to indolizidines

This paper describes the establishment of a new synthetic route to the hydrobromide salt of (+)-coniceine 1 with high enantiopurity in five steps and 8% overall yield. The key step is the reductive photocyclization of an acyclic chiral dienamide, for which a convenient one-pot synthesis is described...

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Veröffentlicht in:Tetrahedron: asymmetry 2007-03, Vol.18 (5), p.671-678
Hauptverfasser: Hjelmgaard, Thomas, Gardette, Daniel, Tanner, David, Aitken, David J.
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
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Zusammenfassung:This paper describes the establishment of a new synthetic route to the hydrobromide salt of (+)-coniceine 1 with high enantiopurity in five steps and 8% overall yield. The key step is the reductive photocyclization of an acyclic chiral dienamide, for which a convenient one-pot synthesis is described.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2007.03.004