A facile route to the pentacyclic lamellarin skeleton via Grob reaction between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1,3,3-trimethyl-3,4-dihydroisoquinolines |
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| Authors: | Vladislav Yu Korotaev Igor B Kutyashev Yurii V Shklyaev |
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| Institution: | a Department of Chemistry, Ural State University, pr. Lenina, 51, 620083 Ekaterinburg, Russia
b Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 614600 Perm, Russia |
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| Abstract: | The basic structural framework of lamellarin alkaloids, 8,9-dihydro-6H-chromeno4′,3′:4,5]pyrrolo2,1-a]isoquinoline derivatives, has been obtained in good yields via Grob reaction between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1,3,3-trimethyl-3,4-dihydroisoquinolines in refluxing isobutanol. When the reaction was carried out in toluene at room temperature, only Michael adducts, as a mixture of two diastereomers, were isolated. |
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| Keywords: | Lamellarin skeleton Grob reaction 3-Nitro-2-(trifluoromethyl)-2H-chromenes 1 3 3-Trimethyl-3 4-dihydroisoquinolines |
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