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A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction |
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| Authors: | Fedor I Zubkov Julya D Ershova Vladimir P Zaytsev Alexandr S Peregudov Roman S Borisov Abel M Maharramov |
| Institution: | a Organic Chemistry Department, Russian Peoples Friendship University, 6 Miklukho-Maklaya Street, Moscow 117198, Russian Federation b Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, Moscow 119991, Russian Federation c A.V. Topchiev Institute of Petrochemical Synthesis, 29 Leninsky prospekt, Moscow 119991, Russian Federation d Baku State University, 23 Z. Khalilov Street, Baku AZ-1148, Azerbaijan |
| Abstract: | The interaction between 1-furyl-1,2,3,4-tetrahydroisoquinolines and unsaturated acids derivatives (acryloyl, methacryloyl, and crotonoyl chloride, maleic and citraconic anhydride) was studied. It was shown that the reaction proceeds via amide formation and subsequent intramolecular Diels-Alder reaction of the furan (IMDAF). The 4+2] cycloaddition proceeded under mild reaction conditions (25-80 °C) and afforded only the exo-adduct in a high yield. With this method, a new approach to the isoindolo1,2-a]isoquinoline system, the basic structural element of alkaloids Jamtine, Hirsutine, and Nuevamine, is proposed. |
| Keywords: | Intramolecular Diels-Alder reaction of furan (IMDAF) Isoindolo[1 2-a]isoquinolines 1-Furyltetrahydroisoquinolines Alkaloids Jamtine Hirsutine |
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