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Beilstein J. Org. Chem. 2013, 9, 537–543, doi:10.3762/bjoc.9.59
Graphical Abstract
Scheme 1: Retrosynthetic plan.
Scheme 2: Preparation of 2.
Scheme 3: Generation of 3 by lithium–bromine exchange.
Scheme 4: Cascade products.
Figure 1: Reaction progress of the attempted triple-cyclization cascade.
Scheme 5: Proton transfer that foils final cyclization.
Scheme 6: Preparation of iodide 7 and an authentic sample of 5.
Scheme 7: Evidence for the intermolecular nature of the formal [1,4]-proton transfer.