title: Synthesis of polyhydroxylated quinolizidine and indolizidine scaffolds from sugar-derived lactams via a one-pot reduction/Mannich/Michael sequence.
abstract: A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz's reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky's diene. The stereochemical course of the investigated reaction has been explained in detail. The obtained bicyclic products are attractive building blocks for the synthesis of various naturally occurring polyhydroxylated alkaloids and their derivatives.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Szcześniak
authors.forename: Sebastian
authors.initials: S
authors.lastname: Stecko
authors.forename: Elżbieta
authors.initials: E
authors.lastname: Maziarz
authors.forename: Olga
authors.initials: O
authors.lastname: Staszewska-Krajewska
authors.forename: Bartłomiej
authors.initials: B
authors.lastname: Furman
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams; D008958:Models, Molecular; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D002241:Carbohydrates; D054836:Indolizidines; D007769:Lactams; D054837:Quinolizidines