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 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.
Song
Ling
L
Department of Chemistry, University of New Mexico, Albuquerque, New Mexico 87131, USA.
Duesler
Eileen N
EN
Mariano
Patrick S
PS
D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D010777:Photochemistry; D011726:Pyridinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007212:Indolizines; D011726:Pyridinium Compounds