title: An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine.
abstract: The synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of α-aminoallene 17 is described. The target molecule was synthesized in 13 linear steps from Cbz-protected Garner aldehyde (R)-2 in an overall yield of 2.4%. The approach was first examined in model studies, which afforded the alkylated azafuranomycin derivative 13a in 2.9% yield over 12 steps.
authors.affiliation: Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany.
authors.forename: Jörg
authors.initials: J
authors.lastname: Erdsack
authors.forename: Norbert
authors.initials: N
authors.lastname: Krause
keywords: allenes; amino acids; cuprates; furanomycin; gold catalysis