Terry Rosen

The synthesis of mevinic acids

Article de synthese en 3 parties: synthese totale des mevinoline et compactine; synthese des fragments «hexaline» et «octaline» des composes precedents et de leurs derives dihydrogenes; synthese de la partie lactone

Acyclic stereoselection. 21. Synthesis of an ionophore synthon having four asymmetric carbons by sequential aldol addition, claisen rearrangement and hydroboration

Abstract Allylic alcohol 7, obtained by a synthesis involving stereoselective aldol addition to an unsaturated aldehyde, is transformed by the Ireland variant of the Claisen rearrangement into unsaturated acid 9. Subsequent elaboration of this material gives homoallylic alcohols 13 and 14, which are hydroborated to obtain primarily 3 and 4. It is shown that the hydroboration is intermolecular, rather than intramolecular.

Synthesis and biological activity of the hexalin moiety of compactin (ML-236B)

Abstract Alcohols 14 and 21 and the derived half-glutarate esters 15 and 22 have been prepared and evaluated as inhibitors of HMG CoA reductase. Compound 14 , the hexalin moiety of the natural fungal metabolite compactin (ML-236B) and compound 21 , its isomeric diene, have essentially no inhibitory properties. Compounds 15 and 22 show definite activity, although several orders of magnitude lower than that shown by compactin.