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Beilstein J. Org. Chem. 2012, 8, 1630–1636, doi:10.3762/bjoc.8.186
Graphical Abstract
Scheme 1: Conditions for the cyclization of 2’-hydroxycinnamate and related precursors to coumarins. (a) Ther...
Scheme 2: Hypothetical catalytic cycle: Nucleophile-assisted cyclization of (E)-ethyl 2’-hydroxycinnamate (1)...
Scheme 3: Proposed catalytic cycle, based on 31P NMR spectroscopic and color evidence.
Beilstein J. Org. Chem. 2012, 8, 1112–1117, doi:10.3762/bjoc.8.123
Figure 1: Furocoumarins.
Scheme 1: Synthesis of smyrindiol (1) by Grande et al.
Scheme 2: Synthesis of smyrindiol by Snider et al.
Scheme 3: Proline-catalyzed intramolecular aldol reaction of O-acetonyl-salicylaldehydes.
Scheme 4: First retrosynthetic analysis.
Scheme 5: Attempted proline catalyzed aldol reaction.
Scheme 6: Second retrosynthetic analysis.
Scheme 7: Asymmetric total synthesis of smyrindiol (1).