Stereoselective Synthesis of Polyhydroxylated Indolizidines Based on Pyridinium Salt Photochemistry and Ring Rearrangement Metathesis

Ruthenium-catalyzed ring rearrangement metathesis (RRM) reactions of stereochemically diverse, differentially protected 4-N-allylacetamidocyclopenten-3,5-diols, prepared by using pyridinium salt photochemistry, have been explored as part of a program to develop novel routes for the synthesis of poly...

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Published inJournal of organic chemistry Vol. 69; no. 21; pp. 7284 - 7293
Main Authors Song, Ling, Duesler, Eileen N, Mariano, Patrick S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.10.2004
Amer Chemical Soc
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Summary:Ruthenium-catalyzed ring rearrangement metathesis (RRM) reactions of stereochemically diverse, differentially protected 4-N-allylacetamidocyclopenten-3,5-diols, prepared by using pyridinium salt photochemistry, have been explored as part of a program to develop novel routes for the synthesis of polyhydroxylated indolizidines. The RRM reactions, which produce selectively protected 1-acetyl-2-allyl-3-hydroxy-1,2,3,6-tetrahydropyridines, were found to take in high yields and with high levels of regioselectivity. The significance of RRM reactions of 4-N-allylacetamidocyclopenten-3,5-diols in the context of polyhydroxylated indolizidine synthesis is demonstrated by an application to the concise preparation of the potent glycosidase inhibitor, (−)-swainsonine.
Bibliography:istex:284AD136E92A10EB964D43BCC0F003723B8F81B0
ark:/67375/TPS-62PL5GTW-0
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo040226a