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

作者：Korotaev Vladislav Yu; Sosnovskikh Vyacheslav Ya^*; Kutyashev Igor B; Barkov Alexey Yu; Shklyaev Yurii V

来源：Tetrahedron Letters, 2008, 49(37): 5376-5379.

DOI：10.1016/j.tetlet.2008.06.122

• lamellarin skeleton
• Grob reaction
• 3-nitro-2-(trifluoromethyl)-2H-chromenes
• 1,3,3-trimethyl-3,4-dihydroisoquinolines

The basic structural framework of lamellarin alkaloids, 8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-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.

• 出版日期2008-9-8