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Synthesis and Biological Evaluation of 1‐Deoxy‐5‐hydroxysphingosine Derivatives
Author(s) -
Esteve Judit,
Lorente Adriana,
Romea Pedro,
Urpí Fèlix,
RíosLuci Carla,
Padrón José M.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001268
Subject(s) - enantiopure drug , chemistry , diastereomer , aldol reaction , ketone , diol , stereochemistry , transformation (genetics) , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , gene
A sequential transformation based on the titanium‐mediated aldol addition of ( S )‐1‐bromo‐3‐( tert ‐butyldimethylsilyloxy)‐2‐butanone, a chiral lactate‐derived ketone, to tetradecanal followed by reduction of the ensuing aldolate afforded the corresponding syn ‐1,3‐diol as a single diastereomer. Debromination and further manipulation of this intermediate allowed the efficient synthesis of two enantiopure 1‐deoxy‐5‐hydroxysphingosines, which exhibit promising biological activity against a representative panel of human cancer lines.