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Stereoselective Synthesis of Swainsonines from Pyridines

Heimgärtner, Gerres, Raatz, Dirk and Reiser, Oliver (2005) Stereoselective Synthesis of Swainsonines from Pyridines. Tetrahedron 61 (3), pp. 643-655.

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Other URL: http://dx.doi.org/10.1016/j.tet.2004.10.086


An efficient synthesis of (−)-swainsonine and (−)-2,8a-di-epi-swainsonine was developed starting from readily available 2-pyridinecarbaldehyde and 3-hydroxypyridine. In particular, it was demonstrated that the mixture of simple indolizidines, i.e. lentiginosine and epi-lentiginosine, being readily available by a number of different synthetic routes, can be directly converted to swainsonine.

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Item type:Article
Date:17 January 2005
Institutions:Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
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Keywords:Indolizidines; Swainsonine; 2,8a-Di-epi-swainsonine; Pyridine-N-oxides; Asymmetric dihydroxylation
Dewey Decimal Classification:500 Science > 540 Chemistry & allied sciences
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Unknown
Item ID:354
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