Skip to main page content
Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
, 79 (21), 10487-503

Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds From Sugar-Derived Lactams via a One-Pot reduction/Mannich/Michael Sequence

Affiliations

Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds From Sugar-Derived Lactams via a One-Pot reduction/Mannich/Michael Sequence

Piotr Szcześniak et al. J Org Chem.

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.

Similar articles

See all similar articles

Publication types

LinkOut - more resources

Feedback