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Séminaire Chimie ED459

Enantiopure bioactive amino alcohols from natural amino acids – Fact or fiction ?

Prof. Ari M. P. Koskinen (Laboratory of Organic Chemistry, Department of Chemistry, Helsinki University of Technology, Finland)

publié le , mis à jour le

Le Mercredi 24 Février 2010 à 13h45
ENSCM Amphithéâtre Chaptal

Nature provides us with a wonderful pool of enantiopure starting materials for synthesis : amino acids, sugars and many (but not all !) terpenes can be isolated even in large quantities in an uncompromised 100% ee. Vicinal amino alcohols constitute a versatile group of organic structures ; they are, in principle, available in enantiopure form from the chiral pool compounds or through chiral catalysis ; they are potent intermediates for the synthesis of natural products and medicinally/biologically active compounds, and they provide a highly desirable scaffold for the construction of ligands for metals as well as organocatalysts as. These new techniques will open up valuable new possibilities for the invention of new technologies for chemical synthesis, the desired course of chemical discoveries for the future. A robust entry to enantiopure vicinal amino alcohols from inexpensive naturally occurring amino acids has therefore become a key challenge for our endeavours in the development of methodology.

For the past two decades, we have been involved in the development of syntheses of natural products from naturally occurring amino acids, and in the course of these studies we have every now and then had the opportunity to investigate the synthesis of vicinal amino alcohol for various purposes. We have employed mainly two alternative strategies.

The more traditional one is based on the diastereoselective alkylation of amino aldehydes, whereas the alternative strategy is based on our original discovery that γ-chiral β-keto phosphonates can be converted to the corresponding enones via a Horner-Wadsworth-Emmons (HWE) olefination without epimerisation. Reductive operations on the alkene and/or diastereoselective reduction of the carbonyl functionality was considered as the suitable route to the amino alcohols.


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