Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
Carlos Díez‐Poza, Laura Fernández-Peña, Paula González-Andrés, Asunción Barbero
Abstract
Developing new procedures for the synthesis of tetrahydropyrans in a very stereoselective manner is of great importance for the synthesis of THP-containing natural products. Here, we report an interesting protocol for the synthesis of polysubstituted halogenated tetrahydropyrans by silyl-Prins cyclization of vinylsilyl alcohols, in which the nature of the Lewis acid determines the outcome of the process. The methodology has been applied to the synthesis of a known antinociceptive.
Topics & Concepts
Prins reactionSilylationChemistryLewis acids and basesStereoselectivityEnantioselective synthesisTotal synthesisCombinatorial chemistryOrganic chemistryCatalysisStereochemistrySynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisChemical synthesis and alkaloids