277744-70-4Relevant academic research and scientific papers
Synthesis of macrolide-saccharide hybrids by ring-closing metathesis of precursors derived from glycitols and benzoic acids
Matos, Marie-Christine,Murphy, Paul V.
, p. 1803 - 1806 (2007/10/03)
The benzomacrolactone structural motif is a privileged or evolutionarily selected scaffold that codes properties required for binding to proteins and novel analogues thereof may provide a source of new bioactive compounds. Saccharides are also privileged structures, with (amino)sugars, imino-sugars, and sugar amino acids being applied as scaffolds for the development of nonpeptidal peptidomimetics. The syntheses of novel polyhydroxylated oxamacrolides, structural analogues of natural polyketide derived macrolides, are described herein, providing a basis for their development as scaffolds. The syntheses were carried out from benzoic acids and appropriately protected D-mannitol or D-sorbitol (D-glucitol). Ring-closing metathesis was applied in the macrocyclization step with high E-alkene selectivities being observed. X-ray crystal structures, for two polyhydroxylated derivatives, show that the macrocyclic rings display similar conformations. In addition, intermolecular hydrogen-bonding networks are observed in the lattices.
Ruthenium carbene complexes with imidazol-2-ylidene ligands: Syntheses of conduritol derivatives reveals superior RCM activity
Ackermann, Lutz,El Tom, David,Fürstner, Alois
, p. 2195 - 2202 (2007/10/03)
Syntheses of conduritol A, E and F derivatives are described using galactitol, D-mannitol and D-glucitol, respectively, as the starting materials. The key steps of this approach comprise a Tebbe olefination reaction for the preparation of dienes 15, 21 and 27 followed by ring closing metathesis (RCM) for the formation of the polyhydroxylated cyclohexene rings of the targets. A comparative study shows that the latter transformation is best achieved with catalytic amounts of ruthenium carbene complex 3a bearing one PCy3 and one 2,3-dihydro-1H-imidazol-2-ylidene ligand in its coordination sphere. (C) 2000 Elsevier Science Ltd.
