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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
Authors
Ershova J.D.
Khrustalev V.N.
+6 more
Matiychuk V.S.
Obushak M.D.
Sokolova E.A.
Varlamov A.V.
Zaytsev V.P.
Zubkov F.I.
Publication date
Publisher
'Elsevier BV'
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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 isoindolo[1, 2-a]isoquinoline alkaloids jamtine and hirsutine. © 2010 Elsevier Ltd. All rights reserved
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Last time updated on 05/11/2022