The intramolecular Diels–Alder vinylfuran (IMDAV) reaction: a short approach to aza-analogues of pinguisane-type sesquiterpenes. Issue 30 (22nd July 2015)

• Record Type: Journal Article
• Authors: Horak, Yuriy I.; Lytvyn, Roman Z.; Homza, Yuriy V.; Zaytsev, Vladimir P.; Mertsalov, Dmitriy F.; Babkina, Maria N.; Nikitina, Eugenia V.; Lis, Tadeusz; Kinzhybalo, Vasyl; Matiychuk, Vasyl S.; Zubkov, Fedor I.; Varlamov, Alexey V.; Obushak, Mykola D.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 30(2015)
• Page Start: 4499
• Page End: 4501
• Publication Date: 2015-07-22
• Subjects: QUBLWRWLSVIEBB-QVXRUGPVSA-N -- LUXJIYDEDCQDHW-KPXOXKRLSA-N -- GDJLUGXITFZWTD-KPXOXKRLSA-N -- DECJYQJWUXGXOY-QCZZGDTMSA-N -- KWUPRZDZHHHKTL-VBNZEHGJSA-N -- PPQALUZZMCMVKR-NZVBXONLSA-N -- WQEQVBRDUDKSDT-KNXALSJPSA-N -- UHOVQNZJYSORNB-UHFFFAOYSA-N -- PRUASMFMBMPYRX-QVXRUGPVSA-N -- VHCXZFVEVPNQQF-ZTQXTMOCSA-N -- OBJUYIBWPNMFGL-IOSSYPJHSA-N -- PLPXREOZJNDREU-QVXRUGPVSA-N; Furan -- [2+4] cycloaddition -- Diels–Alder reaction -- IMDAV -- Furo[2, 3-f]isoindoles -- Pinguisane-type sesquiterpenes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.115
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.