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Biomedical subjects

Pierre Van de Weghe

Publications and source records attributed to Pierre Van de Weghe.

6 recordsLinked to original sources
PubMed2005

Controlled synthesis of cis or trans isomers of 1,3-disubstituted tetrahydroisoquinolines and 2,5-disubstituted pyrrolidines.

[reactions: see text] The stereoselective outcome of Pd(II)- or Ag(I)-catalyzed intramolecular N-alkylation to afford 1,3-disubstituted 1,2,3,4-tetrahydroisoquinolines was examined. In the absence of additional substituents, Pd(II) allows a facile access to the cis isomers, while Ag(I) favors formation of the trans isomers. The same observation was made for the synthesis of 2,5-disubstituted pyrrolidines. Possible reasons for the observed stereoselectivities are discussed.

Journal Article↗
PubMed2005

Enantioselective approaches to potential MetAP-2 reversible inhibitors.

[reaction: see text] Enantioselective deprotonation of 4-substituted cyclohexanones and highly stereoselective conjugate addition of higher order mixed cuprates were the key steps in a concise synthesis of fumagalone-related molecules. The origin of the (low) biological activity of the new compounds as compared to fumagalone is briefly discussed.

Aminopeptidases↗
PubMed2005

The application of olefin metathesis to the synthesis of biologically active macrocyclic agents.

Recent developments of the metathesis reaction in the area of biologically active molecules are presented. Scope and limitations of ring-closing metathesis to form medium and large rings are discussed and illustrated by the epothilone synthesis. Applications of the metathesis reaction related to medicinal chemistry, including solid phase synthesis and combinatorial chemistry are presented.

Alkenes↗
PubMed2004

MetAP-2 inhibitors based on the fumagillin structure. Side-chain modification and ring-substituted analogues.

The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

Aminopeptidases↗