title: Amidopalladation of alkoxyallenes applied in the synthesis of an enantiopure 1-ethylquinolizidine frog alkaloid.
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.
authors.affiliation: Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands.
authors.forename: Sape S
authors.initials: SS
authors.lastname: Kinderman
authors.forename: René
authors.initials: R
authors.lastname: De Gelder
authors.forename: Jan H
authors.initials: JH
authors.lastname: Van Maarseveen
authors.forename: Hans E
authors.initials: HE
authors.lastname: Schoemaker
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes