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First total synthesis of the pyrrolizidine alkaloid amphorogynine C through intramolecular azide-olefin cycloaddition

AuthorsMiguel, Irene de ; Velado, Marina ; Herradón García, Bernardo ; Mann, Enrique
Issue Date2012
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry: 4347- 4353 (2012)
AbstractThe first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen-Johnson rearrangement and an intramolecular azide-olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis. The first synthesis of the representative pyrrolizidine alkaloid amphorogynine C is described. The key step includes an intramolecular azide-olefin cycloaddition reaction. The proposed structure of the natural product was confirmed by single-crystal X-ray diffraction analysis. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.201200384
Identifiersdoi: 10.1002/ejoc.201200384
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(IQOG) Artículos
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