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Synthesis of 7-hydroxy-6H-benzo[c]chromen-6-ones based on a ‘[3+3] cyclization/domino retro-Michael-aldol-lactonization’ strategy |
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| Authors: | Ehsan Ullah Bettina Appel Peter Langer |
| Affiliation: | a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, D-18059 Rostock, Germany b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, D-18059 Rostock, Germany c Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany |
| Abstract: | The TiCl4-mediated [3+3] cyclization of 2,4-bis(trimethylsilyloxy)penta-1,3-diene with 3-silyloxyalk-2-en-1-ones afforded 2-acetylphenols, which were transformed into functionalized chromones. The Me3SiOTf-mediated condensation of the latter with 1,3-bis(silyl enol ethers) and subsequent domino ‘retro-Michael-aldol-lactonization’ reaction afforded 7-hydroxy-6H-benzo[c]chromen-6-ones. |
| Keywords: | Chromones Cyclizations Domino reactions Oxygen heterocycles Silyl enol ethers |
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