Asymmetric Synthesis of Two Hydroxylated Pyrrolizidines From a C-Allyl Epoxypyrrolidine

Abstract

The efficient two-step preparation of a new pivotal C-allyl epoxypyrrolidine intermediate from an enantio-enriched epoxyaldehyde precursor is described. The synthetic potential of this building block is demonstrated with the first enantioselective synthesis of two hydroxylated pyrrolizidine relying on a regio- and stereocontrolled epoxide opening reaction.

GRAPHICAL ABSTRACT

Keywords:

• Asymmetric synthesis
• epoxide
• iminosugars
• pyrrolizidine