Published in
Elsevier, Tetrahedron Letters, 30(56), p. 4499-4501
DOI: 10.1016/j.tetlet.2015.05.115
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The intramolecular Diels–Alder vinylfuran (IMDAV) reaction: a short approach to aza-analogues of pinguisane-type sesquiterpenes
Journal article published in 2015 by
Yuriy I. Horak 
,
Roman Z. Lytvyn,
Yuriy V. Homza,
Vladimir P. Zaytsev,
Dmitriy F. Mertsalov,
Maria N. Babkina,
Eugenia V. Nikitina,
Tadeusz Lis,
Vasyl Kinzhybalo ,
Vasyl S. Matiychuk,
Fedor I. Zubkov,
Alexey V. Varlamov,
Mykola D. Obushak
,
Roman Z. Lytvyn,
Yuriy V. Homza,
Vladimir P. Zaytsev,
Dmitriy F. Mertsalov,
Maria N. Babkina,
Eugenia V. Nikitina,
Tadeusz Lis,
Vasyl Kinzhybalo ,
Vasyl S. Matiychuk,
Fedor I. Zubkov,
Alexey V. Varlamov,
Mykola D. Obushak
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Abstract
The reaction of readily accessible (3-furyl)allylamines with maleic anhydride, followed by a domino sequence involving acylation/cycloaddition/proton shift steps, led to the formation of furo[2,3-f]isoindoles - the aza-analogs of pinguisane-type sesquiterpenes. The key intramolecular Diels-Alder vinylfuran (IMDAV) reaction proceeded under mild conditions, with high levels of diastereoselectivity and satisfactory yields.