Synthesis of a versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block and its application for the stereoselective synthesis of N-homoceramides

A versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block has been synthesized starting from D-isoascorbic acid, a common food preservative. The key transformation in this approach was the introduction of branching through a high yield and fully regioselective epoxide opening. This flexible synthon has been elaborated to a new class of (dihydro-)N-homo(phyto)ceramides

Patent developments in antimycobacterial small-molecule therapeutics

At. present, clinical management of patients infected with Mycobacterium tuberculosis faces difficult problems, such as the worldwide emergence of multidrug resistant tuberculosis (MDR-TB), and the increase in AIDS-associated infections. Development of new drugs with greater or distinct anti-mycobacterial activity than those currently used is, therefore, urgently desired. Three main strategies toward this effort are pursued: discovery of new targets; structural modification of existing antibiotics; and identification of natural resources for novel antibiotics

Synthesis of 5-substituted 2'-deoxyuridine-5'-phosphonate analogues and evaluation of their antiviral activity

A small series of 5-(hetero)aryl-modified nucleoside phosphonates was synthesized via an 8-step procedure including a Wittig reaction and Suzuki-Miyaura coupling. An unanticipated anomerization during phosphonate deprotection allowed us to isolate both anomers of the 5-substituted 2'-deoxy-uridine phosphonates and assess their antiviral activity against a broad panel of viruses