2-Benzoylamino-2-deoxy-2-hydroxymethyl-D-mannonic (6) and -D-gluconic (13) acids have been synthesized from D-fructose by the following route: (i) a hydrocyanation reaction of fructosyl-p-tolylamine, (ii) acid hydrolysis of the nitrile produced, and (iii) hydrogenolysis of the tolylamino group then formed. The stereochemistry of the hydrocyanation reaction has been studied by changing both the solvents and other reaction conditions. The major (gluconic) and the minor (mannonic) epimers have been separated and characterized by chemical and spectroscopic methods. Upon N-acylation the amino acids (6) and (13) cyclized to the corresponding 1,4-lactones (5) and (12). One of these 2-benzoylamino-2- deoxy-2-hydroxymethyl-D-hexono-1,4-lactones [the mannonic (5)], was transformed in six steps into the 2-benzoylamino-2-benzoyloxymethyl-2-deoxy-3-O-benzoyl-5-O- (4-tolylsulphonyl)-D-lyxono-1,4-lactone (3), which is a key intermediate in the convergent total synthesis of the antibiotic thermozymocidin (1).
2-Benzoylamino-2-deoxy-2-hydroxymothyl-D-hexono-1,4-lactones: Synthesis from D-fructose and utilization in the total synthesis of thermozymocidin (myriocin) / L. Banfi, M.G. Beretta, L. Colombo, C.M.A. Gennari, C. Scolastico. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - (1983), pp. 1613-1619.
|Titolo:||2-Benzoylamino-2-deoxy-2-hydroxymothyl-D-hexono-1,4-lactones: Synthesis from D-fructose and utilization in the total synthesis of thermozymocidin (myriocin)|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||1983|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1039/P19830001613|
|Appare nelle tipologie:||01 - Articolo su periodico|