A Base-Catalyzed, Domino Aldol/hetero-Diels–Alder Synthesis of Tricyclic Pyrano[3,4‑c]chromenes in Glycerol
The domino aldol/hetero-Diels–Alder synthesis of some new tricyclic pyrano[3,4-c]chromene derivatives has been achieved successfully after assembling a variety of acyclic or cyclic monoketones with prenyl ether-tethered aldehydes in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in glycerol a...
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Veröffentlicht in: | Journal of organic chemistry 2016-06, Vol.81 (12), p.4955-4964 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | The domino aldol/hetero-Diels–Alder synthesis of some new tricyclic pyrano[3,4-c]chromene derivatives has been achieved successfully after assembling a variety of acyclic or cyclic monoketones with prenyl ether-tethered aldehydes in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in glycerol at 120 °C. The hitherto unreported stereochemical outcome of this synthetic sequence was studied and established on the basis of single-crystal X-ray diffraction data and 2D NMR NOESY spectroscopy along with the isolation and characterization of the intermediate Aldol condensation product. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.6b00107 |