59414-23-2Relevant articles and documents
Synthesis of polyhydroxylated quinolizidine and indolizidine scaffolds from sugar-derived lactams via a one-pot reduction/Mannich/Michael sequence
Szczesniak, Piotr,Stecko, Sebastian,Maziarz, Elzbieta,Staszewska-Krajewska, Olga,Furman, Bartlomiej
, p. 10487 - 10503 (2015/02/19)
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.
Efficient Synthesis of Siloxy Dienes from α,β-Unsaturated Ketones
Hansson, Lars,Carlson, Rolf
, p. 188 - 192 (2007/10/02)
A novel method for the preparation of siloxy dienes has been developed.The reaction system was established by a multivariate screening experiment, where catalysts and solvents were selected according to their principal properties.The best system was lithium bromide-chlorotrimethylsilane-triethylamine in tetrahydrofuran.Optimum experimental conditions were determined by response surface methods.The following substrates were used: 2-butenone, 4-methyl-3-penten-2-one, 4-methoxy-3-buten-2-one, 1-acetylcyclohexene, 2-cyclohexenone, 2-cyclopentenone, 4-phenyl-3-buten-2-one, 4-(4-methoxyphenyl)-3-buten-2-one, and 4,4-dimethyl-2-cyclohexenone.Isolated yields were in the range of 82 - 96percent.