Tagged: fumagillol

CMLD Researchers Publish Paper on “Remodeling” Natural Products in Nature Chemistry

November 7th, 2011 in Beeler, Aaron, CMLD, Front Page, Porco, John, Publications, Snyder, John

CMLD-BU researchers Bradley Balthaser, Meghan Maloney, Aaron Beeler, John Porco & John Snyder, in a paper published in the journal Nature Chemistry [23 OCTOBER 2011 | DOI: 10.1038/NCHEM.1178], present a new approach to accessing new, biorelevant structures by “remodeling” natural products. In this case, they demonstrate how the natural product derivative fumagillol can been remodeled to access a collection of new molecules using highly efficient chemical reactions.

a, Selective formation of perhydroisoindoles, perhydroisoquinolines or morpholinones with phenylalanine as a reaction partner: (i) phenylalanine (2.0 equiv.), M(OTf)n (50 mol%), DTBMP (1.5 equiv.), toluene, 60 °C; (ii) NaOH (2.0 M), tetrahydrofuran, room temperature, 6 h. DTBMP, 2,6-di-tert-butyl-4-methylpyridine; Phe, phenylalanine. b, Molecular models of phenylalanine-derived morpholinones 18 and 21.

a, Selective formation of perhydroisoindoles, perhydroisoquinolines or morpholinones with phenylalanine as a reaction partner: (i) phenylalanine (2.0 equiv.), M(OTf)n (50 mol%), DTBMP (1.5 equiv.), toluene, 60 °C; (ii) NaOH (2.0 M), tetrahydrofuran, room temperature, 6 h. DTBMP, 2,6-di-tert-butyl-4-methylpyridine; Phe, phenylalanine. b, Molecular models of phenylalanine-derived morpholinones 18 and 21.

More

Tagged , ,