Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 50, Pages 18280-18289Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503171
Keywords
domino reactions; microwave chemistry; organocatalysis; synthetic methods; total synthesis
Categories
Funding
- Spanish Ministerio de Economia y Competitividad (MINECO)
- European Regional Development Fund [CTQ2011-28417-C02-02, CTQ2013-45415-P]
- UPV/EHU [UFI11/22 QOSYC]
- Basque Government (GV/EJ) [IT-324-07]
- Spanish MEC
- CSIC
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The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-break ing conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6p electrocyclization, and an aromatization reaction.
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