Total Synthesis of Uniflorine A, Casuarine, Australine, 3-epi-Australine, and 3,7-Di-epi-australine from a Common Precursor

A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2010-02, Vol.75 (3), p.815-824
Hauptverfasser:	Ritthiwigrom, Thunwadee, Willis, Anthony C, Pyne, Stephen G
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Catalysis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indolizines - chemical synthesis Indolizines - chemistry Magnetic Resonance Spectroscopy Molecular Structure Organic chemistry Preparations and properties Pyrroles - chemical synthesis Pyrroles - chemistry Pyrrolizidine Alkaloids - chemical synthesis Pyrrolizidine Alkaloids - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo902355p