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Beilstein J. Org. Chem. 2013, 9, 860–865, doi:10.3762/bjoc.9.99
Graphical Abstract
Scheme 1: Our first- [26] and second-generation [27] approaches to (−)-agelastatin A (1).
Scheme 2: The present iron(II)-mediated aminohalogenation of N-tosyloxycarbamate 8 providing key intermediate...
Scheme 3: Aminohalogenation of azidoformate 3 (2 g scale) under FeBr2/Bu4NBr conditions.
Figure 1: Byproducts formed by aminohalogenation of N-tosyloxycarbamate 8 with FeCl2/TMSCl in EtOH (see Table 1; ent...
Scheme 4: Plausible reaction pathways in the aminohalogenation of N-tosyloxycarbamate 8 with FeX2/Bu4NX.
Scheme 5: Plausible reaction pathway to produce compounds 9 and 10.