Synthetic Studies toward Highly Functionalized 5β-Lanosterol Derivatives:  A Versatile Approach Utilizing Anionic Cycloaddition

Stereoselective synthesis of the potentially biologically valuable 5β-lanosteroidal-type backbone was achieved via anionic cycloaddition. Synthesis of the two new bicyclic Nazarov intermediates 14 and 40 and their cycloaddition with chiral cyclohexenone 25 and further functional group manipulations...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-08, Vol.71 (16), p.6149-6156
Main Authors: Ramachandran, Sreekanth A, Kharul, Rajendra K, Marque, Sylvain, Soucy, Pierre, Jacques, Frédéric, Chênevert, Robert, Deslongchamps, Pierre
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Steroids
Terpenoids
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Summary:Stereoselective synthesis of the potentially biologically valuable 5β-lanosteroidal-type backbone was achieved via anionic cycloaddition. Synthesis of the two new bicyclic Nazarov intermediates 14 and 40 and their cycloaddition with chiral cyclohexenone 25 and further functional group manipulations resulted in highly functionalized tetracyclic intermediates 28 and 44. These synthetic intermediates could lead to the total synthesis of new lanosterol-based inhibitors.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0608725