2-Substituted-3,7-dinitro-11-oxatricycloundec-9-ene: an approach towards the synthesis of Ergot alkaloids

2-Substituted-3,7-dinitro-11-oxatricycloundec-9-ene: an approach towards the synthesis of Ergot alkaloids

A simple and versatile method for the preparation of various ergoline or secoergoline skeleton, using 2-substituted-3,7-dinitro-11-oxatricycloundec-9-ene as key intermediates, is described. The key step involves an IMDAF reaction with an excellent stereocontrol. This novel synthetic route provides n...

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Bibliographic Details
Published in:Tetrahedron Vol. 60; no. 23; pp. 5105 - 5110
Main Authors: Mahmood, Shatha Younis, Lallemand, Marie-Christine, Sader-Bakaouni, Lina, Charton, Olivier, Vérité, Philippe, Dufat, Hanh, Tillequin, François
Format: Journal Article
Language:English
Published: Elsevier Ltd 31-05-2004
Subjects:
Ergoline
Ergot alkaloids
IMDAF
Lysergic acid
Oxatricycloundec-9-ene compounds
Secoergoline
Ergoline
Oxatricycloundec-9-ene compounds
Secoergoline
Ergot alkaloids
Lysergic acid
IMDAF
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Description
Summary:A simple and versatile method for the preparation of various ergoline or secoergoline skeleton, using 2-substituted-3,7-dinitro-11-oxatricycloundec-9-ene as key intermediates, is described. The key step involves an IMDAF reaction with an excellent stereocontrol. This novel synthetic route provides new cycloadducts as useful scaffolds for Ergot alkaloids synthesis. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.03.091