Journal
TETRAHEDRON
Volume 65, Issue 18, Pages 3789-3803Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.02.024
Keywords
Intramolecular Diels-Alder reaction of furan (IMDAF); Isoindolop[1,2-a]isoquinolines; 1-Furyltetrahydroisoquinolines; Alkaloids; Jamtine; Hirsutine
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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 degrees C) and afforded only the exo-adduct in a high yield. With this method, a new approach to the isoindolo[1,2-a]isoquinoline system, the basic structural element of alkaloids Jamtine, Hirsutine, and Nuevamine, is proposed. (C) 2009 Elsevier Ltd. All rights reserved.
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