Synthesis 2018; 50(21): 4295-4300
DOI: 10.1055/s-0037-1609582
paper
© Georg Thieme Verlag Stuttgart · New York

Facile, Stereocontrolled Synthetic Route towards Bis-functionalised Pyrrolizidines

Marcin Lindner
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland   Email: Jurczak_group@icho.edu.pl
,
Antoni Krasiński
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland   Email: Jurczak_group@icho.edu.pl
,
Janusz Jurczak*
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland   Email: Jurczak_group@icho.edu.pl
› Author Affiliations
Further Information

Publication History

Received: 22 May 2018

Accepted after revision: 19 June 2018

Publication Date:
23 July 2018 (eFirst)

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.

Supporting Information

 
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