1-Deoxy-5-hydroxysphingolipids as New Anticancer Principles:  An Efficient Procedure for Stereoselective Syntheses of 2-Amino-3,5-diols

Enantioselective preparation of the linear homoallylic alcohol I allows efficient formation of the 2-amino-3,5-diol moiety present in several biologically active compounds, including 1-deoxy-5-hydroxysphingosine analogue IV, which has exhibited excellent biological activity against colon cancer. The...

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Bibliographic Details
Published in:Organic letters 2005-07, Vol.7 (15), p.3155-3157
Main Authors: Wiseman, John M, McDonald, Frank E, Liotta, Dennis C
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - pharmacology
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Catalysis
Glycosphingolipids - chemistry
Glycosphingolipids - pharmacology
Molecular Structure
Stereoisomerism
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Summary:Enantioselective preparation of the linear homoallylic alcohol I allows efficient formation of the 2-amino-3,5-diol moiety present in several biologically active compounds, including 1-deoxy-5-hydroxysphingosine analogue IV, which has exhibited excellent biological activity against colon cancer. The conversion of I into IV involves a sequence of enantioselective epoxidation of the O-tert-butoxycarbonyl derivative of I, followed by regioselective and stereospecific oxacyclization of II to introduce differentiated oxygens in III.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050829o