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The first example of an intramolecular Diels-Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1,2-a]isoquinoline core of the jamtine and hirsutine alkaloids |
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| Authors: | Fedor I Zubkov Julya D Ershova Mykola D Obushak Ekaterina A Sokolova Alexey V Varlamov |
| Institution: | a Organic Chemistry Department, Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation b Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine c Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow 119991, Russian Federation |
| Abstract: | 1-(2-Furyl)-3,4-dihydroisoquinolines, easily prepared from readily available phenethylamines, undergo tandem alkylation/4+2]-cycloaddition with allyl halides. The reaction proceeds via 2-allyl-1-furyl-3,4-dihydroisoquinolinium salt formation and subsequent intramolecular exo-Diels-Alder reaction of furan with the allyl fragment (IMDAF reaction). The adducts formed include the basic structural element of the isoindolo1,2-a]isoquinoline alkaloids jamtine and hirsutine. |
| Keywords: | Intramolecular Diels-Alder furan reaction IMDAF Alkaloids jamtine Hirsutine Isoindolo[1 2-a]isoquinoline |
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