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Organosilicon intermediates towards aza-bioactive targets

Ziel



The aim of this project is the development of new approaches to aza-bioactive targets. In particular, the synthesis of b-,g- and d-lactams with the emphasis on (lactam-derived antibiotics is planned. The strategy to be developed is based on previous results about N-alkylidene-bis(trimethylsilyl)methylamines as a new series of stable imines. These imines on treatment with aminoketene synthons and further chemical elaboration of the resulting cycloadducts should provide a route to monobactams and related, b-lactam antibiotics.

The first step of the synthesis will be performed by using the Evans-Sjogren ketenes, but other aminoketene synthons derived from ty- and o-lactams will also be studied to improve the stereochemical course of the cycloaddition reaction. The g- and d-lactams will be prepared through substitution reactions carried out on the corresponding N-trimethylsilyl and N-[(chlorodimethylsilyl)methyl]-lactams. The synthesis of lactamopeptides and N-methyl a-amino acids from these lactams will also be explored in conjunction with a route to b-lactamoketones.

In parallel with these approaches to a-amino acids and related derivatives, the synthesis of a-amino acid-N-carboxy anhydrides from b-lactams is also envisaged. The reaction sequence consists of a a-hydroxylation of the corresponding a-amino b-lactam followed by Baeyer-Villiger oxidation of the resulting a-keto-b-lactam

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Koordinator

Universidad del Pais Vasco
EU-Beitrag
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Adresse
Manuel Lardizabal - App. 1072 3
20080 San Sebastian
Spanien

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