Amalia M. Estévez

A short overview on the medicinal chemistry of (-)-shikimic acid.

Shikimic acid, a natural compound is a key intermediate in the biosynthesis of amino acids. Consequently, this derivative is widely present in many plants and has interesting biological properties. But besides the pharmacological relevance of shikimic acid itself, it is also an intermediate in the synthesis of many drugs, being the most relevant the antiviral agent oseltamivir (Tamiflu™). Here we present a short overview on recent natural, biotechnological and synthetical sources of shikimic acid, togheter with pharmacological applications of this compound and a selection of derivatives, including oseltamivir (Tamiflu™).

Indium-mediated allylation and Reformatsky reaction on glyoxylic oximes under ultrasound irradiation

A novel and more convenient method for the indium-promoted allylation of glyoxylic oximes based on the use of ultrasonic waves is reported. A similar procedure was used to develop the first example reported in the literature of an indium-mediated Reformatsky reaction on oxime ethers.

6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology.

In the search for alternative non-metabolizable inducers in the l-rhamnose promoter system, the synthesis of fifteen 6-deoxyhexoses from l-rhamnose demonstrates the value of synergy between biotechnology and chemistry. The readily available 2,3-acetonide of rhamnonolactone allows inversion of configuration at C4 and/or C5 of rhamnose to give 6-deoxy-d-allose, 6-deoxy-d-gulose and 6-deoxy-l-talose. Highly crystalline 3,5-benzylidene rhamnonolactone gives easy access to l-quinovose (6-deoxy-l-glucose), l-olivose and rhamnose analogue with C2 azido, amino and acetamido substituents. Electrophilic fluorination of rhamnal gives a mixture of 2-deoxy-2-fluoro-l-rhamnose and 2-deoxy-2-fluoro-l-quinovose. Biotechnology provides access to 6-deoxy-l-altrose and 1-deoxy-l-fructose.

An overview of key routes for the transformation of sugars into carbasugars and related compounds

This chapter reports an overview of the most relevant routes developed for the transformation of sugars into carbasugars and related compounds.

Protocol for the Incorporation of γ-Amino Acids into Peptides: Application to (−)-Shikimic Acid Based 2-Amino-Methylcyclohexanecarboxylic Acids

The first example of a new protocol for the incorporation of γ-amino acids into peptides is reported. It involved a shikimic acid based stereoselective synthesis polyhydroxylated-2-nitromethylcyclohexanecarboxylic acids, which were directly incorporated into peptides.

Recent advances in nitro sugar chemistry

This chapter reports the most relevant recent contributions in nitro sugar chemistry. It includes the following aspects: preparation of nitro sugars, formation of carbon–carbon bonds and transformation of the nitro group into other functionalities.