Expedient pyrrolizidine synthesis by propargylsilane addition to N-acyliminium ions followed by gold-catalyzed alpha-allenyl amide cyclization

Arjen C Breman; Jan Dijkink; Jan H van Maarseveen; Sape S Kinderman; Henk Hiemstra

doi:10.1021/jo901393y

Expedient pyrrolizidine synthesis by propargylsilane addition to N-acyliminium ions followed by gold-catalyzed alpha-allenyl amide cyclization

J Org Chem. 2009 Aug 21;74(16):6327-30. doi: 10.1021/jo901393y.

Authors

Arjen C Breman¹, Jan Dijkink, Jan H van Maarseveen, Sape S Kinderman, Henk Hiemstra

Affiliation

¹ Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands.

PMID: 20560574
DOI: 10.1021/jo901393y

Abstract

A reaction sequence, involving the addition of (substituted) propargylsilanes to lactam-derived N-acyliminium ions followed by gold-catalyzed cyclization of the resulting alpha-allenyl amide, is applied in expedient syntheses of pyrrolizidine alkaloids heliotridine and ent-retronecine in five steps from (S)-malic acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Catalysis
Cyclization
Gold / chemistry*
Imines / chemistry*
Kinetics
Lactams / chemistry
Pyrrolizidine Alkaloids / chemical synthesis*
Pyrrolizidine Alkaloids / chemistry
Silanes / chemistry*

Substances

Amides
Imines
Lactams
Pyrrolizidine Alkaloids
Silanes
Gold