131423-59-1Relevant articles and documents
Towards a New Type of HMG-CoA Reductase Inhibitors: Part II: Dramatic Substituent Effects in the C-5 Epimerisation of Carbohydrate Derivatives
Bocquel, P.,Taillefumier, C.,Chapleur, Y.,Renaut, P.,Samreth, S.,Bellamy, F. D.
, p. 83 - 96 (2007/10/02)
In the course of our search for a new class of HMG-CoA reductase inhibitors, the synthesis of reaction intermediate analogues was investigated.Compound 2, having the C-5 (R) configuration of natural mevinic acids, was prepared in enantiomerically pure form starting from levoglucosan.During this synthesis, an epimerisation of the olefinic intermediate 16 was observed and was found to depend strongly both on the axial or equtorial orientation and on the nature of the C-3 substituent.Biological activity of compound 2 is reported.Keywords: HMGCoA reductase, inhibitor, carbohydrate, base catalyzed epimerisation, O-silyl protecting group.
Towards a new type-of HMG-COA reductase inhibitor
Barth,Bellamy,Renaut,Samreth,Schuber
, p. 6731 - 6740 (2007/10/02)
In an attempt to design a novel class of HMG-Co A reductase inhibitors, we have synthesized compound as a reaction intermediate analogue of the enzymatic reduction of mevaldic acid by NADPH. A 15 steps, enantioselective sequence allowed us, from commercial R-(+)-malic acid to prepare aldehyde in an optically pure form and to couple it with the nicotinamide moiety affording the target molecule.
