Published as part of the Special Topic Heterocycles as Catalysts, Ligands, and Targets
Abstract
A simple and convenient method for the synthesis of bis-functionalised pyrrolizidines
starting from readily available N-Cbz-l-prolinal is described. This aldehyde was converted within two concise steps to the
corresponding aminoepoxides, which were separately subjected to regioselective cyclisation
induced by a reductive cleavage of the Cbz protecting group. The versatile and concise
strategy holds great potential for practical application in the straightforward preparation
of pyrrolizidine-based drugs and natural products.
Key words
alkaloids - heterocycles - diastereoselective synthesis - asymmetric epoxidation -
cyclisation - tandem reaction