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Beilstein J. Org. Chem. 2017, 13, 2833–2841, doi:10.3762/bjoc.13.275
Graphical Abstract
Figure 1: Molecular structures of AL-12, AL-12B and AL-5.
Scheme 1: Retrosynthetic analysis of AL-12, AL-12B and AL-5 (in their neutral forms) and their derivatives.
Scheme 2: Optimization study using phenylacetate 2a.
Scheme 3: Photodecarboxylative additions to N-(bromoalkyl)phthalimides.
Figure 2: Crystal structures of photoaddition products 3a (left) and 3b (right).
Scheme 4: Formation of 5 by photodecarboxylative additions.
Scheme 5: Acid-catalyzed dehydration of 3a–q.
Figure 3: Crystal structure of (E)-7a. Side view and front view.
Scheme 6: Amination of dehydrated products 7a–q.
Figure 4: Crystal structure of (Z)-8a. Side view and front view.
Scheme 7: Mechanistic scenario for the photodecarboxylative addition.
Scheme 8: Possible scenarios for nucleophilic cyclization to 4.
Scheme 9: Possible E/Z isomerization for compounds 8a–y.