The stereoselective synthesis of ( E)-alkene dipeptide isosteres

A diastereo- and enantio-selective synthesis of the ( E)-alkene dipeptide isostere of l-Ala- l-Ala from l-alanine has been developed which proceeds via stereocontrolled addition of a ( Z)-vinyllithium reagent followed by a [2,3]-Wittig rearrangement. The synthesis proceeds in seven steps overall fro...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1993-12, Vol.3 (12), p.2879-2882
Main Authors: Yong, Yaw Fui, Lipton, Mark A.
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:A diastereo- and enantio-selective synthesis of the ( E)-alkene dipeptide isostere of l-Ala- l-Ala from l-alanine has been developed which proceeds via stereocontrolled addition of a ( Z)-vinyllithium reagent followed by a [2,3]-Wittig rearrangement. The synthesis proceeds in seven steps overall from l-alanine methyl ester. It is believed that this approach will provide a fairly general and convenient route to isosteres of a number of different dipeptides. Graphic
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)80783-6