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Beilstein J. Org. Chem. 2015, 11, 1503–1508, doi:10.3762/bjoc.11.163
Graphical Abstract
Figure 1: Retrosynthetic analysis of tricyclic amide 1.
Scheme 1: Synthesis of tricyclic ketone 4.
Scheme 2: Beckmann rearrangement of oximes 8a and 8b.
Scheme 3: Beckmann rearrangement reaction in a single step.
Scheme 4: Synthesis of ring-rearrangement precursors.
Scheme 5: Synthesis of Beckmann rearrangement precursors.
Scheme 6: Beckmann rearrangement of oxime isomers 11a and 11b.
Figure 2: Molecular crystal structure of compound 11b.
Scheme 7: Synthesis of aza tricyclic compound 1 by RRM.
Beilstein J. Org. Chem. 2015, 11, 1259–1264, doi:10.3762/bjoc.11.140
Figure 1: Commercially available ruthenium catalysts used in RRM metathesis.
Figure 2: Crystal structure of 5 with thermal ellipsoids drawn at 50% probability level.
Scheme 1: Synthesis of hexacyclic compound 6a by using an RRM approach.
Scheme 2: Synthesis of hexacyclic compound 11 by using an RRM route.