Amidopalladation of alkoxyallenes applied in the synthesis of an enantiopure 1-ethylquinolizidine frog alkaloid

Sape S Kinderman; René De Gelder; Jan H Van Maarseveen; Hans E Schoemaker; Henk Hiemstra; Floris P J T Rutjes

doi:10.1021/ja039919j

Amidopalladation of alkoxyallenes applied in the synthesis of an enantiopure 1-ethylquinolizidine frog alkaloid

J Am Chem Soc. 2004 Apr 7;126(13):4100-1. doi: 10.1021/ja039919j.

Authors

Sape S Kinderman¹, René De Gelder, Jan H Van Maarseveen, Hans E Schoemaker, Henk Hiemstra, Floris P J T Rutjes

Affiliation

¹ Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands.

PMID: 15053587
DOI: 10.1021/ja039919j

Abstract

A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidine structural motif, which is a key synthon in the synthesis of the naturally occurring poisonous frog quinolizidine 233A and derivatives such as the 1-epi-isomer of quinolizidine 207I.