Title of article
A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction
Author/Authors
Fedor I. Zubkov، نويسنده , , Julya D. Ershova، نويسنده , , Anna A. Orlova، نويسنده , , Vladimir P. Zaytsev، نويسنده , , Eugeniya V. Nikitina، نويسنده , , Alexandr S. Peregudov، نويسنده , , Atash V. Gurbanov، نويسنده , , Roman S. Borisov، نويسنده , , Victor N. Khrustalev، نويسنده , , Abel M. Maharramov، نويسنده , , Alexey V. Varlamov، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2009
Pages
15
From page
3789
To page
3803
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 isoindolo[1,2-a]isoquinoline system, the basic structural element of alkaloids Jamtine, Hirsutine, and Nuevamine, is proposed.
Keywords
jamtine , 2-a]isoquinolines , Alkaloids , Hirsutine , Intramolecular Diels–Alder reaction of furan (IMDAF) , 1-Furyltetrahydroisoquinolines
Journal title
Tetrahedron
Serial Year
2009
Journal title
Tetrahedron
Record number
1095392
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