The objectives of the proposed research are to use in organic synthesis the ability of transition metals to activate aromatic substrates toward nucleophilic addition. Two main areas of endeavor will be studied: (1) Chromium tricarbonyl complexes of alkoxybenzene derivatives, in which the alkoxy group is chiral, will be used as substrates for asymmetric carbon nucleophile addition reactions. The outcome of this protocol is the formation of chiral substituted cyclohexenones in high enantiomeric excess. (2) Cyclopentadienylruthenium complexes of chloroarenes will be used to effect nucleophilic aromatic substitution as a key step in the total synthesis of the aglycone of ristocetin A, which is a complex peptido aryl ether related to the important glycopeptide antibiotics vancomycin and teicoplanin.
| Paramahamsan, Harinandini; Pearson, Anthony J; Pinkerton, Nathalie M et al. (2008) 1,5-Asymmetric induction during nucleophilic additions to arenetricarbonylchromium complexes: tricarbonyl(eta(6)-1-methyl-4-{spiro[(1R,2S)-1,7,7-trimethylbicyclo[2.2.1]heptane-3,2'-1,3-dioxolan]-2-yloxy}benzene)chromium. Acta Crystallogr C 64:m147-8 |
| Pearson, Anthony J; Ciurea, Diana V (2008) Synthesis of a key precursor for orienticin C and model study on ruthenium-mediated macrocyclization. J Org Chem 73:760-3 |
| Pearson, Anthony J; Ciurea, Diana V; Velankar, Avdhoot (2008) Studies toward the total synthesis of ristocetin A aglycone using arene-ruthenium complexes as S(N)Ar substrates: Construction of an advanced tricyclic intermediate. Tetrahedron Lett 49:1922-1926 |
| Pearson, A J; Hwang, J J (2000) Preparation of donor-sigma-acceptor molecules using arene-ruthenium chemistry. J Org Chem 65:3466-72 |
